Bittersweet World

In November 2006, after completing her run as Roxie Hart in the London production of the musical Chicago, Simpson said that she was going to meet with record executives soon to begin work on her third album.{{Cite news |date=15 November 2006 |title=For The Record: Quick News On Michael Jackson, Beyonce, Chris Brown, Ashlee, Cure, Clipse, Nicky Hilton & More |url=https://www.mtv.com/news/1545866/for-the-record-quick-news-on-michael-jackson-beyonce-chris-brown-ashlee-cure-clipse-nicky-hilton-more/ |archive-url=https://web.archive.org/web/20210125102216/http://www.mtv.com/news/1545866/for-the-record-quick-news-on-michael-jackson-beyonce-chris-brown-ashlee-cure-clipse-nicky-hilton-more/ |url-status=dead |archive-date=January 25, 2021 |access-date=October 5, 2007 |agency=MTV News}} Geffen Records chairman Ron Fair said in early December that plotting Simpson's musical direction would be "very tricky" because of press scrutiny, but that he would work with Simpson to overcome industry doubts about her musical credibility "because she deserves to be heard and she deserves a shot."{{Cite web |last= |first= |date=December 6, 2006 |title=For The Record: Quick News On Gwen, Good Charlotte, Christina, Katharine McPhee, Ashlee, Rihanna & More |website= MTV|url=http://www.mtv.com/news/1547396/for-the-record-quick-news-on-gwen-good-charlotte-christina-katharine-mcphee-ashlee-rihanna-more/ |url-status=dead |archive-url=https://web.archive.org/web/20140906204449/http://www.mtv.com/news/1547396/for-the-record-quick-news-on-gwen-good-charlotte-christina-katharine-mcphee-ashlee-rihanna-more/ |archive-date=September 6, 2014 |access-date=October 5, 2007 |agency=MTV News}}{{Cite magazine |last=Kheraj |first=Alim |date=November 14, 2018 |title=ashlee simpson knows she's underrated, but she's okay with that |url=https://i-d.co/article/ashlee-simpson-interview/ |access-date=September 10, 2021 |magazine=i-D}}

In March 2007, Simpson said her next album would have "a more soulful sound" and that she was writing with a wider group of artists in comparison to her previous albums.{{Cite news |date=March 6, 2007 |title=For The Record: Quick News On Mariah, Jennifer Hudson, Jay-Z, Ashlee, K-Fed, Lily Allen, Chili Peppers & More |url=http://www.mtv.com/news/1553956/for-the-record-quick-news-on-mariah-jennifer-hudson-jay-z-ashlee-k-fed-lily-allen-chili-peppers-more/ |url-status=dead |archive-url=https://web.archive.org/web/20220417072639/http://www.mtv.com/news/1553956/for-the-record-quick-news-on-mariah-jennifer-hudson-jay-z-ashlee-k-fed-lily-allen-chili-peppers-more/ |archive-date=17 April 2022 |access-date=5 October 2007 |agency=MTV News}} Later that month, Simpson was reportedly writing with Timbaland, Kenna and Chad Hugo.{{Cite magazine |last=Greenblatt |first=Leah |date=March 25, 2007 |title=Ashlee Simpson teaming up with Robert Smith? |url=https://ew.com/article/2007/03/25/ashlee-simpson-teaming-robert-smith/ |url-status=dead |archive-url=https://web.archive.org/web/20151125220435/https://ew.com/article/2007/03/25/ashlee-simpson-teaming-robert-smith/ |archive-date=November 25, 2015 |access-date=October 5, 2007 |magazine=Entertainment Weekly |language=en}} She was also said to be working with John Legend, Beth Hart, and Tim Rice-Oxley of Keane. Though it was initially reported that Simpson was also working with The Cure frontman Robert Smith, both parties later denied a collaboration.{{Cite news |date=July 20, 2007 |title=Jessica Simpson Says Ashlee Is A Thriftier Shopper; Plus 50 Cent, Kelly Clarkson, Ne-Yo, Lindsay Lohan & More, In For The Record |url=http://www.mtv.com/news/1565236/jessica-simpson-says-ashlee-is-a-thriftier-shopper-plus-50-cent-kelly-clarkson-ne-yo-lindsay-lohan-more-in-for-the-record/ |url-status=dead |archive-url=https://web.archive.org/web/20220823002719/https://www.mtv.com/news/7lctng/jessica-simpson-says-ashlee-is-a-thriftier-shopper-plus-50-cent-kelly-clarkson-ne-yo-lindsay-lohan-more-in-for-the-record |archive-date=August 23, 2022 |access-date=October 5, 2007 |agency=MTV News}}

Although Simpson said her sound would stay in the pop rock realm, she also mentioned that her music was evolving and would have less emphasis on relationship troubles and breakups. She clarified, "This record is not like 'I didn't steal your boyfriend' or anything like that."{{Cite magazine |last=Malcom |first=Shawna |date=May 17, 2007 |title=Ashlee Simpson: Girl on Fire |magazine=Cosmopolitan |url=https://www.cosmopolitan.com/entertainment/celebs/news/a1781/ashlee-simpson/ |url-status=live |access-date=September 12, 2021 |archive-url=https://web.archive.org/web/20151209024722/https://www.cosmopolitan.com/entertainment/celebs/news/a1781/ashlee-simpson/ |archive-date=December 9, 2015}} Simpson expressed feeling less pressure to be successful with her third album, considering her previous two albums had already achieved chart success. She told CosmoGirl,

This time, I didn't feel like I have to prove myself—that's all behind me. I have a stronger vision for this record...I was able to challenge myself by stepping out of the box I was in and working with new sounds and new people. That ultimately yielded different results than what people might expect from me. This is a fun party album, and I get to be kind of cheeky for the first time...silly and quirky."[http://carrieborzillo.com/wp-content/uploads/2015/06/CosmoGirl-Ashlee-Simpson-Cover-Story.pdf Ashlee Simpson: The Survivor]", CosmoGirl, December 2007/January 2008. p 107. Retrieved September 12, 2021.

Simpson told MTV News in December 2007 the album's title would be Bittersweet World, which is also the name of one of the album's songs.{{Cite web |last=Montgomery |first=James |date=2007-12-19 |title=Ashlee Simpson Reveals Christmas Gifts For Fans (New Album Title) And Pete Wentz (Shh!) |url=http://www.mtv.com/news/1576807/ashlee-simpson-reveals-christmas-gifts-for-fans-new-album-title-and-pete-wentz-shh/ |url-status=dead |archive-url=https://web.archive.org/web/20220626151447/http://www.mtv.com/news/1576807/ashlee-simpson-reveals-christmas-gifts-for-fans-new-album-title-and-pete-wentz-shh/ |archive-date=2022-06-26 |access-date=2007-12-19 |website=MTV News |language=en}} She previously considered the title Color Outside the Lines, a line from the song "Rule Breaker". She described the title Bittersweet World as reflecting how she "feel[s] about the world right now" and later said that the song itself is "about how with the bad comes the good in pretty much every situation and vice versa. There are hard things, but you always have to find the positive."{{Cite web |date=7 February 2008 |title=Ashlee Simpson chat transcript |url=http://www.teenmusic.com/events.asp?s=transcript&id=104 |url-status=dead |archive-url=https://web.archive.org/web/20080210075814/http://www.teenmusic.com/events.asp?s=transcript&id=104 |archive-date=10 February 2008 |access-date=8 February 2008 |website=TeenMusic.com}} Simpson did the photoshoot for the album with photographer Ben Watts in Los Angeles.{{Cite web|title=Bittersweet World - Ashlee Simpson {{!}} Album Credits|url=https://www.allmusic.com/album/bittersweet-world-mw0000581373/credits|website=AllMusic}} The photoshoot took place while Simpson still had blonde hair; she subsequently dyed it red in January 2008.{{Cite news |date=January 11, 2008 |title=Ashlee Debuts New 'Do Outside Koo Koo Roo |work=X17 Online |url=https://www.x17online.com/celebrities/ashlee_simpson/ashlee_debuts_new_do_outside_koo_koo_roo-01112008.php |url-status=dead |access-date=April 5, 2008 |archive-url=https://web.archive.org/web/20080112202346/https://www.x17online.com/celebrities/ashlee_simpson/ashlee_debuts_new_do_outside_koo_koo_roo-01112008.php |archive-date=12 January 2008}}

For Bittersweet World, Simpson worked with hit producers like Timbaland, King Logan of The Royal Court, Chad Hugo of The Neptunes, Kenna, Jack Joseph Puig, Jim Beanz, and J-Roc.{{Cite news |last=Vineyard |first=Jennifer |date=9 September 2007 |title=Ashlee Simpson's Bad-Girl Alter Ego Rules New Timbaland-Produced Album |work=MTV News |url=http://www.mtv.com/news/articles/1569231/20070909/index.jhtml |url-status=dead |access-date=2007-10-05 |archive-url=https://web.archive.org/web/20080309152759/http://www.mtv.com/news/articles/1569231/20070909/index.jhtml |archive-date=9 March 2008}} John Shanks returned as producer, in addition to Simpson's collaborative partner and band guitarist Ray Brady, who introduced Simpson to the sounds of 1980s band Missing Persons.{{Cite news |date=15 January 2008 |title=Ashlee Simpson Has A New Single; New Album Almost Complete |work=Starpulse |url=http://www.starpulse.com/news/index.php/2008/01/15/ashlee_simpson_has_a_new_single_new_albu |url-status=dead |access-date=2008-01-16 |archive-url=https://web.archive.org/web/20080117052123/http://www.starpulse.com/news/index.php/2008/01/15/ashlee_simpson_has_a_new_single_new_albu |archive-date=17 January 2008}} Timbaland, who "tapped into Simpson's love of '80s music,"{{Cite magazine |last=Cohen |first=Jonathan |date=2007-12-07 |title=Ashlee Goes 'Surreal' For New Video |url=https://www.billboard.com/music/music-news/ashlee-goes-surreal-for-new-video-1047110/ |url-status=live |archive-url=https://archive.today/20220823003833/https://www.billboard.com/music/music-news/ashlee-goes-surreal-for-new-video-1047110/ |archive-date=2022-08-23 |access-date=2007-12-07 |magazine=Billboard}} worked on six songs, while others were guided by Hugo and Kenna. Two tracks, "Outta My Head (Ay Ya Ya)" and "Ragdoll", were written with indie artist Santigold. "Murder" originally featured a rap from Gym Class Heroes frontman Travie McCoy, but he was replaced by Izza Kizza on the album version. "Little Miss Obsessive", a pop rock power ballad, is a duet with Tom Higgenson of the Plain White T's.{{Cite web |last=Fletcher |first=Alex |date=2008-07-25 |title=Ashlee Simpson: 'Little Miss Obsessive' |url=http://www.digitalspy.com/music/single-reviews/a115276/ashlee-simpson-little-miss-obsessive/ |url-status=live |archive-url=https://web.archive.org/web/20210912002849/https://www.digitalspy.com/music/single-reviews/a115276/ashlee-simpson-little-miss-obsessive/ |archive-date=2021-09-12 |access-date=2021-09-12 |website=Digital Spy |language=en-GB}}

Simpson wrote or co-wrote all of the album's songs, saying "This is my art and it's personal. If someone else writes the song without my input, it doesn't feel honest." At the 2007 MTV Video Music Awards, Simpson gave MTV a sneak peek of the album, describing the sound as being more beat-based in contrast to her previous guitar-driven sound. Simpson revealed the record was completed in November 2007, but that she was also continuing to write in anticipation of a March 2008 release.{{Cite web |last=Vineyard |first=Jennifer |date=2007-11-13 |title=Ashlee Simpson Talks About Her 'Highs And Lows,' New LP At CosmoGirl! Awards |url=http://www.mtv.com/news/1574211/ashlee-simpson-talks-about-her-highs-and-lows-new-lp-at-cosmogirl-awards/ |url-status=dead |archive-url=https://web.archive.org/web/20210913103426/http://www.mtv.com/news/1574211/ashlee-simpson-talks-about-her-highs-and-lows-new-lp-at-cosmogirl-awards/ |archive-date=2021-09-13 |access-date=2007-11-14 |website=MTV News |language=en}}

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| quote = There's a song on the record called "Bittersweet World." And it is, to me. The song is saying that, and "Why can't we all just get along?" It's a tongue-in-cheek kind of thing, but it really is one of those love-to-hate kind of things.

| source = Simpson talks about the title track "Bittersweet World".{{cite web|url=http://www.starpulse.com/news/index.php/2008/01/24/ashlee_simpson_talks_about_her_new_album |title=Ashlee Simpson Talks About Her New Album 'Bittersweet World', Herself And More |date=2008-01-24 |archive-url=https://web.archive.org/web/20080127145950/http://www.starpulse.com/news/index.php/2008/01/24/ashlee_simpson_talks_about_her_new_album |archive-date=2008-01-27 |url-status=dead |website=Starpulse}}

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Bittersweet World contains influences from '70s and '80s music, particularly synth-pop and new wave. Simpson said she was inspired by women like Chrissie Hynde, Debbie Harry and Pat Benatar, because "they are strong and vulnerable simultaneously, yet they still make you want to dance." The Timbaland-produced "Outta My Head (Ay Ya Ya)" has been compared to the sound of Missing Persons. Simpson said the song is a get-out-of-my-head track, saying, "I just have too many voices in my head, everyone having their own opinion."

"Boys", written with Chad Hugo and Kenna, is a pop disco song.{{Cite news |last=Guerra |first=Joey |date=22 April 2008 |title=Ashlee Simpson's third album is sweet |work=Houston Chronicle |url=https://www.chron.com/entertainment/music/article/Ashlee-Simpson-s-third-album-is-sweet-1633746.php |url-status=live |access-date=April 23, 2008 |archive-url=https://web.archive.org/web/20210224161418/https://www.chron.com/entertainment/music/article/Ashlee-Simpson-s-third-album-is-sweet-1633746.php |archive-date=24 February 2021}} "Boys" was likened to "The Cardigans' 'Lovefool' atop a Chic rhythm",{{Cite magazine |last=Cohen |first=Jonathan |date=2008-03-17 |title=Ashlee Simpson Sets Date For Third Album |url=https://www.billboard.com/music/music-news/ashlee-simpson-sets-date-for-third-album-1046148/ |url-status=live |archive-url=https://archive.today/20220823004724/https://www.billboard.com/music/music-news/ashlee-simpson-sets-date-for-third-album-1046148/ |archive-date=2022-08-23 |access-date=2008-04-05 |magazine=Billboard |language=en-US}} while People called it "the best Kylie Minogue song that Kylie never did".Arnold, Chuck (28 April 2008). Bittersweet World review, People. "Little Miss Obsessive," "Rule Breaker," "What I've Become," and "Ragdoll" stick more to Simpson's rock roots, with "Ragdoll" described as having "a 'Beat It' vibe" and featuring "Casio-esque keyboard tinkling and driving guitars". “Rule Breaker," a "Pat Benatar-like fist-pumper", was named by Rolling Stone as one of the 100 Best Singles of 2008.{{Cite magazine |date=25 December 2008 |title=The 100 Best Singles of 2008 |magazine=Rolling Stone |url=http://www.rollingstone.com/news/story/24947047/the_100_best_singles_of_2008/13 |access-date=17 January 2009 |archive-url=https://web.archive.org/web/20081229022557/http://www.rollingstone.com/news/story/24947047/the_100_best_singles_of_2008/13 |archive-date=29 December 2008}} Of "Rule Breaker," Simpson said it was an attempt to "capture that badass feeling you get sometimes after watching a movie like True Romance. You think you can take on the world and you want to color outside the lines and get a tattoo or mouth off to someone way bigger than you". Rolling Stone noted "What I've Become" as an "excellent coming-of-age anthem" and "a paparazzi kiss-off with an appealingly honest chorus: 'I’ve just begun to find my way.{{'"}}

Billboard characterized "Murder" as having a "dark, hypnotic groove", and being "filled with beats and synth lines". Simpson said the lyrics of "Murder" "aren't serious, based on a true story or a threat....It's a metaphor about a girl who can get away with murder because of who she is." Like "Murder", Simpson has said "Hot Stuff" "is meant to be a fun song.... A lot of things on the record are laughing at situations, poking fun at things. With that, when you go somewhere and girls give you the mean eye. You're like, 'oh, wow – this is crazy.' 'Hot Stuff' makes fun of that. That song is meant to be a good time."{{Cite news |last=D. Amos |first=Joel |title=Ashlee Simpson is 'Hot Stuff' |work=SheKnows |url=http://www.sheknows.com/articles/entertainment/music/803392-Ashlee-Simpson-talks-about-.htm |url-status=dead |access-date=2008-04-11 |archive-url=https://web.archive.org/web/20080414182802/http://www.sheknows.com/articles/entertainment/music/803392-Ashlee-Simpson-talks-about-.htm |archive-date=14 April 2008}}

Simpson co-wrote and co-produced “Never Dream Alone” with Kenna. The song is a spare ballad that is “stripped down to piano, strings, and vocals,” with Simpson citing it as her favorite on the album. The Houston Chronicle said the title track "Bittersweet World" has "the snap-and-wink of a showtune”. According to Simpson, the lyrics are about people coming together and not judging each other".{{Cite news |date=April 21, 2008 |title=Interview with… Ashlee Simpson! |work=Tiger Beat |url=http://www.tigerbeatmag.com/dailydish/category/ashlee-simpson/ |access-date=April 22, 2008 |archive-url=https://web.archive.org/web/20080425032220/http://www.tigerbeatmag.com/dailydish/category/ashlee-simpson/ |archive-date=April 25, 2008}} "No Time for Tears" was described as a "melancholy ballad" that "segues spooky Eurythmics verses into a pop-punk chorus".

Bittersweet World was originally eyed for an October 2007 release and production and recording was reportedly completed that November. However, the actual release date was shifted multiple times, beginning with a delay to the first quarter of 2008.{{Cite web |last= |first= |date=October 15, 2007 |title=Justin Timberlake's Deluxe Sounds; Plus Britney Spears, Lindsay Lohan, 50 Cent, Ashlee Simpson & More, In For The Record |url=http://www.mtv.com/news/1571918/justin-timberlakes-deluxe-sounds-plus-britney-spears-lindsay-lohan-50-cent-ashlee-simpson-more-in-for-the-record/ |archive-url=https://web.archive.org/web/20150210103622/http://www.mtv.com/news/1571918/justin-timberlakes-deluxe-sounds-plus-britney-spears-lindsay-lohan-50-cent-ashlee-simpson-more-in-for-the-record/ |url-status=dead |archive-date=February 10, 2015 |access-date=October 17, 2007 |website=MTV News |language=en}} On February 5, 2008, Simpson released a three-song digital EP, which contained the tracks “Outta My Head (Ay Ya Ya),” “Rule Breaker,” and a track from I Am Me, “Catch Me When I Fall”.{{Cite web |date=23 January 2008 |title=Digital EP Release! |url=http://www.ashleesimpsonmusic.com/news/Default.aspx/pg/3 |url-status=dead |archive-url=https://web.archive.org/web/20080314182659/http://www.ashleesimpsonmusic.com/news/Default.aspx/pg/3 |archive-date=14 March 2008 |access-date=13 September 2021 |website=AshleeSimpsonMusic.com}} Though Bittersweet World's release was expected in March, its new date was revealed to be April 15 as Simpson did promotional radio interviews.Johnjay & Rich radio interview, January 30, 2008. The album was officially released on April 22.

In December 2007, Simpson said she planned to do a “smaller club tour” for the album. The 13-city tour began in January 2008 at the Myst Club in Scottsdale, Arizona, and ended at Mansion in Miami Beach in March.{{Cite web |title=Outta My Head Club Tour |url=http://www.ashlee.com.br/ashlee/tours/outta-my-head-club-tour/ |url-status=dead |archive-url=https://web.archive.org/web/20090106005803/http://www.ashlee.com.br/ashlee/tours/outta-my-head-club-tour/ |archive-date=6 January 2009 |access-date=13 September 2021}} Simpson, accompanied by her guitar player and a DJ,{{Cite news |date=29 January 2008 |title=Ashlee's Mini, Mini Tour Coming Soon |work=PopSugar |url=https://www.popsugar.com/995888 |url-status=dead |access-date=29 January 2008 |archive-url=https://web.archive.org/web/20080129231539/https://www.popsugar.com/995888 |archive-date=29 January 2008}} sang four songs as part of her set—three from Bittersweet World and "L.O.V.E" from I Am Me.{{Cite web |date=25 February 2008 |title=Celebrity Beat: Ashlee Simpson (and Pete Wentz) |url=https://www.chicagomag.com/radar/last-girl-standing/february-2008/celebrity-beat-ashlee-simpson-and-pete-wentz/ |url-status=live |archive-url=https://web.archive.org/web/20210913024414/https://www.chicagomag.com/radar/last-girl-standing/february-2008/celebrity-beat-ashlee-simpson-and-pete-wentz/ |archive-date=13 September 2021 |access-date=13 September 2021 |website=Chicago}} After the tour ended, Simpson spoke of plans of doing a House of Blues tour with her band for the summer.{{Cite web |date=August 2, 2011 |title=Ashlee Simpson Interview at Sauce on February 27, 2008 |url=https://www.youtube.com/watch?v=YVTTFJvJjdg |access-date=September 13, 2021 |website=YouTube}}

Leading up to and following the album’s release, Simpson made in-store appearances at Walmart and appeared on various TV shows, including the Nickelodeon Kids' Choice Awards.{{Cite web |date=20 March 2008 |title=Geffen Records :: Ashlee Simpson's BITTERSWEET WORLD Arrives April 22 |url=http://sev.prnewswire.com/entertainment/20080320/LATH03320032008-1.html |url-status=dead |archive-url=https://web.archive.org/web/20081207232541/http://sev.prnewswire.com/entertainment/20080320/LATH03320032008-1.html |archive-date=7 December 2008 |access-date=5 April 2008 |website=PR Newswire}} Simpson also did promotion in Europe, performing “Outta My Head” on The Paul O’Grady Show[https://www.youtube.com/watch?v=Wy1SiVZ4K5A Ashlee Simpson - "Outta My Head (Ay Ya Ya)" Live on The Paul O'Grady Show]. 26 April 2020 — via YouTube and on BBC Sounds.[https://www.youtube.com/watch?v=5J4ctRbs_nA Ashlee Simpson - Outta My Head @ SOUND]. 24 April 2020 — via YouTube Clothing retailer Wet Seal partnered with Simpson for a collection of tops designed by the singer to coincide with the album's release.{{Cite web |date=27 March 2008 |title=Ashlee Simpson Designs for Wet Seal to Premiere April 22nd |url=http://www.businesswire.com/portal/site/google/?ndmViewId=news_view&newsId=20080327005305&newsLang=en |url-status=dead |archive-url=https://web.archive.org/web/20171201033228/http://www.businesswire.com/portal/site/google/?ndmViewId=news_view&newsId=20080327005305&newsLang=en |archive-date=1 December 2017 |access-date=27 March 2008 |website=Business Wire}} In May 2008, Simpson confirmed her pregnancy,{{Cite web |last=Kaufman |first=Gil |date=29 May 2008 |title=Ashlee Simpson And Pete Wentz Finally Confirm Pregnancy |url=https://www.mtv.com/news/1588256/ashlee-simpson-and-pete-wentz-finally-confirm-pregnancy/ |url-status=dead |archive-url=https://archive.today/20220823011036/https://www.mtv.com/news/l59fkf/ashlee-simpson-and-pete-wentz-finally-confirm-pregnancy |archive-date=2022-08-23 |access-date=2021-09-13 |website=MTV News |language=en}} and summer tour plans were postponed and eventually canceled.{{Cite web|last=|first=|date=2008-06-01|title=Ashlee Simpson : News : "The Dog Ate My Tour"|url=http://www.ashleesimpsonmusic.com/news/default.aspx/nid/14693|url-status=dead|archive-url=https://web.archive.org/web/20080617123743/http://www.ashleesimpsonmusic.com/news/default.aspx/nid/14693|archive-date=2008-06-17|website=AshleeSimpsonMusic.com}}{{Cite web |last= |first= |date=2008-06-01 |title=Ashlee Simpson Postpones Summer Tour Over Pregnancy… Or Album Flop? {{!}} popdirt.com |url=http://popdirt.com/ashlee-simpson-postpones-summer-tour-over-pregnancy-or-album-flop/67668/ |access-date=2021-09-13 |website=Popdirt |language=en-US}}

"Outta My Head (Ay Ya Ya)" was made available for listening on AOL Music on November 30, 2007{{Cite web |last=Davis |first=Kim |date=2007-11-30 |title=Ashlee Simpson, 'Outta My Head' - Song Premiere |url=http://music.aol.com/popeater/2007/11/30/ashlee-simpson-outta-my-head-song-premiere/ |url-status=dead |archive-url=https://web.archive.org/web/20071202000305/http://music.aol.com/popeater/2007/11/30/ashlee-simpson-outta-my-head-song-premiere/ |archive-date=2007-12-02 |access-date=2007-12-01 |website=AOL Music}} and was later released as Bittersweet World's lead single on December 11.{{Cite news |date=2007-11-21 |title=Ashlee Releases "Outta My Head" on December 11 |work=AshleeSimpsonMusic.com |url=http://www.ashleesimpsonmusic.com/news/default.aspx/nid/12249 |url-status=dead |access-date=2007-11-22 |archive-url=https://web.archive.org/web/20071123175653/http://www.ashleesimpsonmusic.com/news/default.aspx/nid/12249 |archive-date=2007-11-23}} Although the song received a positive reception from critics,{{Cite magazine |last=Taylor |first=Chuck |date=12 January 2008 |title=Ashlee Simpson "Outta My Head (Ay Ya Ya)" review |volume=120 |page=40 |magazine=Billboard |issue=2 |url=https://books.google.com/books?id=LRMEAAAAMBAJ&dq=Ashlee+Outta+My+Head&pg=PA40 |access-date=2021-09-13}} it became Simpson's first single to not make the Billboard Hot 100 chart. This was attributed to the synth-pop song being too outside of Simpson's traditional rock sound to resonate with her core fans.{{Cite web |last=Wass |first=Mike |date=17 February 2017 |title=Should Have Been Bigger: Ashlee Simpson's "Outta My Head (Ay Ya Ya)" |url=https://www.idolator.com/7658203/flashback-ashlee-simpson-outta-my-head |url-status=live |archive-url=https://archive.today/20220823011816/https://www.idolator.com/7658203/flashback-ashlee-simpson-outta-my-head?chrome=1 |archive-date=2022-08-23 |access-date=2021-09-13 |website=Idolator}} Though it did not achieve success in the US, it charted in Europe{{Cite web|title=Single - Ashlee Simpson, Outta My Head|url=https://www.offiziellecharts.de/titel-details-404099|website=charts.de}}{{Cite web|title=Official Scottish Singles Sales Chart Top 100|url=https://www.officialcharts.com/charts/scottish-singles-chart/20080525/41/|website=Official Charts Company}}{{Cite web|title=Official Singles Chart Top 100|url=https://www.officialcharts.com/charts/singles-chart/20080525/7501/|website=Official Charts Company}} and Australia.{{Cite web|title="Australian-charts.com – Ashlee Simpson – Outta My Head (Ay Ya Ya)"|url=https://australian-charts.com/showitem.asp?interpret=Ashlee+Simpson&titel=Outta+My+Head+(Ay+Ya+Ya)&cat=s|website=ARIA Top 50 Singles}}

“Little Miss Obsessive” was first played February 21 on Chicago's KISS FM DreX Morning Show.{{Cite web |last=Cady |first=Jennifer |date=2008-02-22 |title=Ashlee Simpson Picks Her Nose at Failed Single |url=https://www.eonline.com/news/62739/ashlee-simpson-picks-her-nose-at-failed-single |url-status=live |archive-url=https://web.archive.org/web/20210913024413/https://www.eonline.com/news/62739/ashlee-simpson-picks-her-nose-at-failed-single |archive-date=2021-09-13 |access-date=2021-09-13 |website=E! Online}} The song, on which Simpson sings with Tom Higgenson of Plain White T's, was more in line with Simpson's pop rock sound,[https://web.archive.org/web/20160914221339/http://www.people.com/people/article/0,,20179306,00.html "Ashlee Simpson Debuts New Song on Chicago Radio"]. People. February 21, 2008. Archived from the [https://web.archive.org/web/20080227110831/http://www.people.com/people/article/0,,20179306,00.html original] on September 14, 2016. Retrieved February 22, 2008. and was subsequently announced as the second single and released on March 11.{{Cite web |date=25 February 2008 |title="Little Miss Obsessive" Released! |url=http://www.ashleesimpsonmusic.com/news/default.aspx/nid/12560 |url-status=dead |archive-url=https://web.archive.org/web/20080302034750/http://www.ashleesimpsonmusic.com/news/default.aspx/nid/12560 |archive-date=2 March 2008 |access-date=27 February 2008 |website=AshleeSimpsonMusic.com}} Though it did not have a music video, "Little Miss Obsessive" charted at number 96 on the Hot 100. Simpson performed "Little Miss Obsessive" on TRL,[https://www.youtube.com/watch?v=gDp6I-DP9kM Ashlee Simpson - "Little Miss Obsessive" Live on TRL]. 11 April 2020 — via YouTube Today,{{Cite news |last=Celizik |first=Mike |date=2008-04-18 |title=Ashlee Simpson dances around pregnancy rumors |work=Today |url=https://www.nbcnews.com/id/wbna23914513 |url-status=live |access-date=2008-04-18 |archive-url=https://web.archive.org/web/20080420234546/http://today.msnbc.msn.com/id/23914513/ |archive-date=2008-04-20}} The Tonight Show with Jay Leno, Ellen Show,[https://www.youtube.com/watch?v=j9Cwti94RnA Ashlee Simpson - Little Miss Obsessive (on Ellen)]. 26 April 2008 — via YouTube Jimmy Kimmel Live!,[https://www.youtube.com/watch?v=U5kMKbu5j38 Ashlee Simpson - Little Miss Obsessive (Live)]. 15 October 2014 —via YouTube and Dance on Sunset.[https://www.youtube.com/watch?v=TVo5cp0ZDZM Ashlee Simpson - "Little Miss Obsessive" Live on Dance On Sunset]. 28 April 2020 — via YouTube

The song "Boys" was speculated to be the third single off the album, due to its promotion in ads and being performed by Simpson on Dancing With the Stars.[https://www.youtube.com/watch?v=zcm0j2PDrtg Ashlee Simpson - Boys (Dancing With The Stars)]. 23 April 2008 —via YouTube Although Simpson stated in a May 2008 interview on a fan club website that "Boys" and "Rule Breaker" would be released as singles, she later stated in an August 2008 interview that "Little Miss Obsessive" would be the last single.

{{Album ratings

| MC = 62/100{{cite web|url=http://www.metacritic.com/music/bittersweet-world|title=Bittersweet World by Ashlee Simpson|website=Metacritic}}

| rev1 = AllMusic

| rev1score = {{rating|4|5}}

| rev2 = The Boston Phoenix

| rev2score = {{Rating|2.5|4}}{{cite web|url=https://thephoenix.com/article_ektid59670.aspx|title=Ashlee Simpson - Bittersweet World|website=The Boston Phoenix|last=Brockman|first=Daniel|date=15 April 2008|access-date=22 March 2025}}

| rev3 = Entertainment Weekly

| rev3score = B

| rev4 = The Guardian

| rev4score = {{Rating|4|5}}{{cite web|url=https://www.theguardian.com/music/2008/may/16/popandrock.shopping2|title=Ashlee Simpson, Bittersweet World|website=The Guardian|last=Macpherson|first=Alex|date=16 May 2008|access-date=22 March 2025}}

| rev5 = Los Angeles Times

| rev5score = {{rating|1.5|4}}{{cite web|url=https://www.latimes.com/archives/la-xpm-2008-apr-22-et-recordrack22-story.html|title=Timbaland is just what Ashlee needs|first=Richard |last=Cromelin |date=22 April 2008 |url-status=live |archive-url=https://web.archive.org/web/20160306053635/http://articles.latimes.com/2008/apr/22/entertainment/et-recordrack22 |archive-date=2016-03-06 |access-date=2011-07-10 |newspaper=LA Times}}

| rev6 = PopMatters

| rev6score = 4/10{{cite web|url=https://www.popmatters.com/ashlee-simpson-bittersweet-world-2496153979.html |title=Ashlee Simpson: Bittersweet World |first=Thomas |last=Hauner |date=13 May 2008 |access-date=2021-09-13 |website=PopMatters}}

| rev7 = Rolling Stone

| rev7score = {{rating|3|5}}

| rev8 = Slant Magazine

| rev8score = {{rating|2.5|5}}{{cite web|url=http://www.slantmagazine.com/music/music_review.asp?ID=1362 |title=Slant Magazine review |author=Cinquemani, Sal |date=2008-04-17 |url-status=dead |archive-url=https://web.archive.org/web/20080421230319/http://www.slantmagazine.com/music/music_review.asp?ID=1362 |archive-date=2008-04-21 |access-date=2008-04-22 |website=Slant Magazine}}

| rev9 = Tom Hull – on the Web

| rev9score = B+ ({{Rating-Christgau|hm2}}){{cite web|url=https://tomhull.com/ocston/nm/get_gl.php?n=Ashlee+Simpson|title=Grade List: Ashlee Simpson|website=Tom Hull – on the Web|first=Hull|last=Tom Hull|access-date=22 March 2025}}

| rev10 = USA Today

| rev10score = {{rating|2|4}}

}}Critical reactions to Bittersweet World were mostly positive. On Metacritic, the album holds a score of 62 out of 100 (indicating "generally favorable reviews”) based on 15 reviews. Much praise was given to the album's dance-pop sound and 1980s-influenced production.Gilbertson, Jon M. (April 22, 2008). "[https://web.archive.org/web/20080426043049/http://www.dallasnews.com/sharedcontent/dws/ent/stories/DN-cdbrief_ashlee_0422gl.State.Edition1.461d60e.html Disc debuts: 'Bittersweet World' by Ashlee Simpson]". Dallas News. Archived from [http://www.dallasnews.com/sharedcontent/dws/ent/stories/DN-cdbrief_ashlee_0422gl.State.Edition1.461d60e.html the original] on April 26, 2008. Retrieved April 23, 2008.{{Cite web |last=Dombal |first=Ryan |title=Blender review |url=http://www.blender.com/guide/reviews.aspx?id=5090 |url-status=dead |archive-url=https://web.archive.org/web/20080501204742/http://www.blender.com/guide/reviews.aspx?id=5090 |archive-date=2008-05-01 |access-date=2021-09-13 |website=Blender}}{{Cite web |last=Farber |first=Jim |date=22 April 2008 |title=Ashlee Simpson's 'Bittersweet World' is back in sync |url=http://www.nydailynews.com/entertainment/music/2008/04/22/2008-04-22_ashlee_simpsons_bittersweet_world_is_bac.html |url-status=dead |archive-url=https://web.archive.org/web/20080426030205/http://www.nydailynews.com/entertainment/music/2008/04/22/2008-04-22_ashlee_simpsons_bittersweet_world_is_bac.html |archive-date=26 April 2008 |access-date=10 July 2011 |website=NY Daily News}} In a three-star review, Rolling Stone said Simpson "skillfully shifts her crunchy, guitar-driven pop to eighties-influenced electro-rock with the help of Timbaland and the Neptunes' Chad Hugo."{{cite web|url=https://www.rollingstone.com/artists/ashleesimpson/albums/album/20256007/review/20256172/bittersweet_world |title=Rolling Stone review |author=Ganz, Caryn |access-date=2008-04-17 |date=2008-05-01 |url-status=dead |archive-url=https://web.archive.org/web/20080421042841/http://www.rollingstone.com/artists/ashleesimpson/albums/album/20256007/review/20256172/bittersweet_world |archive-date=2008-04-21 |magazine=Rolling Stone}}

Stephen Thomas Erlewine wrote, “Where Avril [Lavigne] beat a retreat to the bratty punk-pop that brought her fame, Ashlee has pulled a red hoodie over her head, amped up the dance beats, revved up the '80s retro fetish, and created something that feels of the 2008 moment.”{{cite web|url={{AllMusic|class=album|id=r1346327|pure_url=yes}}|work=AllMusic|author=Erlewine, Stephen Thomas|access-date=July 20, 2010|title=Bittersweet World: Overview}} Entertainment Weekly gave the album a B grade, saying the album is filled with “polished hooks and pretty melodies" and has a "giddy neon energy.”{{cite web |author=Greenblatt, Leah |date=2008-04-18 |title=Bittersweet World |url=https://ew.com/article/2008/04/18/bittersweet-world/ |url-status=live |archive-url=https://web.archive.org/web/20171201132125/https://ew.com/article/2008/04/18/bittersweet-world/ |archive-date=2017-12-01 |access-date=2008-04-20 |magazine=Entertainment Weekly}} The New York Times and People magazine both selected Bittersweet World as a critic’s choice pick,{{Cite web |last=Silverman |first=Stephen M. |date=22 April 2008 |title=Ashlee Simpson's New CD Draws Mixed Reviews |url=http://www.people.com/people/article/0,,20193939,00.html |url-status=dead |archive-url=https://web.archive.org/web/20080423010428/http://www.people.com/people/article/0,,20193939,00.html |archive-date=23 April 2008 |access-date=23 April 2008 |website=People}} with the former saying the music “pays off in songs with crisp beats, teen-seeking choruses and cheerfully obvious lyrics", and that while the album “couldn’t be more calculated, that doesn’t prevent it from being catchy, too.”{{cite web |author=Pareles, Jon |date=2008-04-21 |title=CRITICS' CHOICE; A Rebel With Sharpened Claws |url=http://www.nytimes.com/2008/04/21/arts/music/21choi.html |url-status=dead |archive-url=https://web.archive.org/web/20180430002724/http://www.nytimes.com/2008/04/21/arts/music/21choi.html |archive-date=2018-04-30 |access-date=2008-04-22 |newspaper=The New York Times}}

Digital Spy said it was "easily the best album made by a Simpson sister".{{Cite web |last=Levine |first=Nick |date=2008-05-25 |title=Ashlee Simpson: 'Bittersweet World' |url=http://www.digitalspy.com/music/album-reviews/a96712/ashlee-simpson-bittersweet-world/ |url-status=live |archive-url=https://web.archive.org/web/20190328010456/http://www.digitalspy.com/music/album-reviews/a96712/ashlee-simpson-bittersweet-world/ |archive-date=2019-03-28 |access-date=2011-08-06 |website=Digital Spy |language=en-GB}} Many reviews compared Simpson's music to that of Gwen Stefani.{{Cite magazine |last=Slezak |first=Michael |date=2007-09-18 |title=Snap judgment: Ashlee Simpson's 'Murder' |url=https://ew.com/article/2007/09/18/murder-ashlee-s/ |url-status=live |archive-url=https://archive.today/20220823014250/https://ew.com/tv/steve-martin-retiring-only-murders-in-the-building/ |archive-date=2022-08-23 |access-date=2021-09-13 |magazine=Entertainment Weekly |language=en}} Jill Menze of Billboard praised the album's fun bubblegum sound, but also noted while Bittersweet World "is a party worth attending...not much is missed if your invite got lost in the mail."{{cite web|url=http://www.billboard.com/bbcom/content_display/reviews/albums/e3iaeef0c1a4b682082259c1657d5256d6b |title=Billboard review |author=Menze, Jill |access-date=2008-04-20 |url-status=dead |archive-url=https://web.archive.org/web/20080501013906/http://www.billboard.com/bbcom/content_display/reviews/albums/e3iaeef0c1a4b682082259c1657d5256d6b |archive-date=2008-05-01 |magazine=Billboard}} Negative reviews said Simpson's dabbling in different musical genres resulted in a lack of cohesiveness,{{Cite web|last=Gamboa|first=Glenn|date=22 April 2008|title=Review: Ashlee Simpson's 'Bittersweet World'|url=http://www.newsday.com/entertainment/music/ny-etledew5658389apr22,0,7503523.column|url-status=dead|archive-url=https://web.archive.org/web/20080426231152/http://www.newsday.com/entertainment/music/ny-etledew5658389apr22,0,7503523.column|archive-date=26 April 2008|website=Newsday}} and that Simpson was merely imitating other artists.{{Cite web |last=Davies |first=Evan |date=2008-04-24 |title=Ashlee Simpson |url=https://nowtoronto.com/music/album-reviews/ashlee-simpson-2008-04-24 |url-status=live |archive-url=https://web.archive.org/web/20160122000453/https://nowtoronto.com/music/album-reviews/ashlee-simpson-2008-04-24/ |archive-date=2016-01-22 |access-date=2008-04-25 |website=NOW Magazine |language=en-US}}Gennoe, Dan (June 1, 2008). [https://web.archive.org/web/20080610175027/http://uk.launch.yahoo.com/080601/33/21z35.html "Ashlee Simpson - Bittersweet World"]. Yahoo! Music. Archived from [http://uk.launch.yahoo.com/080601/33/21z35.html the original] on June 10, 2008. Retrieved July 8, 2008.{{cite web|author=D.|first=Spence|date=2008-04-23|title=Ashlee Simpson – Bittersweet World Review - Music Review at IGN|url=http://music.ign.com/articles/868/868895p1.html|url-status=dead|archive-url=https://web.archive.org/web/20110527114248/http://music.ign.com/articles/868/868895p1.html|archive-date=2011-05-27|access-date=2011-08-06|website=IGN|publisher=}} Elysa Gardner of USA Today called Bittersweet World "a collection of bouncy, banal homages to the '80s" and wrote Simpson, "aided by Timbaland, The Neptunes' Chad Hugo and others, channels Debbie Harry, Madonna and Toni Basil about as well as any girl who could afford the help."{{cite web |author=Gardner |first=Elysa |date=2008-04-21 |title=USA Today review |url=http://blogs.usatoday.com/listenup/2008/04/this-weeks-re-2.html |url-status=dead |archive-url=https://web.archive.org/web/20080430070032/http://blogs.usatoday.com/listenup/2008/04/this-weeks-re-2.html |archive-date=April 30, 2008 |access-date=April 23, 2008 |newspaper=USA Today}} Others claimed Simpson lacked the vocal depth to pull off the songs, with Rashod Ollison of The Baltimore Sun writing, "Simpson's colorless voice adds absolutely nothing to the admittedly catchy tracks, which recycle just about every trend heard on mainstream pop radio."Ollison, Rashod (April 22, 2008). [https://web.archive.org/web/20080427004350/http://weblogs.baltimoresun.com/entertainment/critics/blog/2008/04/ashlee_simpson_is_back_as_plas.html "Ashlee Simpson is back, as plastic as ever"]. The Baltimore Sun. Archived from [http://weblogs.baltimoresun.com/entertainment/critics/blog/2008/04/ashlee_simpson_is_back_as_plas.html the original] on April 27, 2008. Retrieved April 27, 2008.{{Cite news |last=Stewart |first=Allison |date=2008-04-22 |title=Ashlee's 'World': Overpopulated And Empty |language=en-US |pages=C01 |newspaper=The Washington Post |url=http://www.washingtonpost.com/wp-dyn/content/article/2008/04/21/AR2008042102804.html |access-date=2008-04-28 |issn=0190-8286}} In a one-star rating, Andy Gill of The Independent wrote,"[Simpson's] voice is all attitude and no emotion, a textbook case of style over substance – and given the paucity of style, that's as insubstantial as it gets."{{cite news |last=Gill |first=Andy |date=May 23, 2008 |title=Album: Ashlee Simpson, Bittersweet World (Geffen) |work=The Independent |url=https://www.independent.co.uk/arts-entertainment/music/reviews/album-ashlee-simpson-bittersweet-world-geffen-832618.html |url-status=dead |access-date=2010-04-26 |archive-url=https://web.archive.org/web/20080608030231/https://www.independent.co.uk/arts-entertainment/music/reviews/album-ashlee-simpson-bittersweet-world-geffen-832618.html |archive-date=2008-06-08}}

Bittersweet World debuted at number four on the U.S. Billboard 200, selling about 47,000 copies in its first week.{{Cite magazine |last=Hasty |first=Katie |date=2008-04-30 |title=Mariah Carey Remains Atop Billboard 200 |magazine=Billboard |url=https://www.billboard.com/articles/news/1045704/mariah-carey-remains-atop-billboard-200 |url-status=live |access-date=2008-04-30 |archive-url=https://web.archive.org/web/20220617104910/https://www.billboard.com/music/music-news/mariah-carey-remains-atop-billboard-200-1045704/ |archive-date=2022-06-17}} This was a much weaker debut than those enjoyed by Autobiography (398,000 copies){{Cite magazine |date=July 28, 2004 |title=Simpson's 'Autobiography' Soars To No. 1 |url=https://www.billboard.com/articles/news/67157/simpsons-autobiography-soars-to-no-1 |url-status=live |archive-url=https://web.archive.org/web/20220426132621/https://www.billboard.com/music/music-news/simpsons-autobiography-soars-to-no-1-67157/ |archive-date=April 26, 2022 |access-date=May 3, 2008 |magazine=Billboard}} and I Am Me (220,000 copies),{{Cite magazine |date=2005-10-26 |title=Simpson Strikes Back: Ashlee Scores 2nd No. 1 |url=https://www.billboard.com/music/music-news/simpson-strikes-back-ashlee-scores-2nd-no-1-60926/ |url-status=live |archive-url=https://web.archive.org/web/20220426133121/https://www.billboard.com/music/music-news/simpson-strikes-back-ashlee-scores-2nd-no-1-60926/ |archive-date=2022-04-26 |access-date=2008-05-03 |magazine=Billboard}} both of which debuted at number one. The album went on to sell 126,000 copies by 2009, her least successful effort to date.{{cite web |last=Goodman |first=Dean |date=2009-04-08 |title=Jessica Simpson's country foray is over |url=http://blogs.reuters.com/world-wrap/2009/04/08/jessica-simpsons-country-foray-is-over/ |url-status=dead |archive-url=https://web.archive.org/web/20160304111851/http://blogs.reuters.com/world-wrap/2009/04/08/jessica-simpsons-country-foray-is-over/ |archive-date=2016-03-04 |access-date=2018-12-04 |website=Reuters}}

{{Track listing

| extra_column = Producer(s)

| headline = Bittersweet World{{nobold| — North American edition}}

| total_length = 39:55

| title1 = Outta My Head (Ay Ya Ya)

| writer1 = {{flat list|

• Ashlee Simpson
• King Logan
• Jerome Harmon
• Dashawn "Happie" White
• Santi White
• Kenna

}}

| extra1 = {{flat list|

• Timbaland
• Logan
• Harmon
• Jim Beanz{{ref|a|[a]}}

}}

| length1 = 3:37

| title2 = Boys

| writer2 = {{flat list|

• Simpson
• Chad Hugo
• Kenna
• Beanz

}}

| extra2 = {{flat list|

• Hugo
• Kenna
• Jack Joseph Puig{{ref|b|[b]}}

}}

| length2 = 3:31

| title3 = Rule Breaker

| writer3 = {{flat list|

• Simpson
• Logan
• Harmon
• Beanz

}}

| extra3 = {{flat list|

• Timbaland
• Logan
• Harmon
• Beanz{{ref|a|[a]}}

}}

| length3 = 3:20

| title4 = No Time for Tears

| writer4 = {{flat list|

• Simpson
• Hugo
• Kenna

}}

| extra4 = {{flat list|

• Hugo
• Kenna

}}

| length4 = 3:36

| title5 = Little Miss Obsessive

| writer5 = {{flat list|

• Simpson
• Beanz
• Victor Valentine
• Karl Berringer

}}

| extra5 = {{flat list|

• Puig
• Berringer
• Beanz{{ref|a|[a]}}

}}

| length5 = 3:42

| title6 = Ragdoll

| writer6 = {{flat list|

• Simpson
• Logan
• Harmon
• S. White
• Beanz

}}

| extra6 = {{flat list|

• Timbaland
• Logan
• Harmon
• Beanz{{ref|a|[a]}}
• Kenna{{ref|a|[a]}}

}}

| length6 = 3:34

| title7 = Bittersweet World

| writer7 = {{flat list|

• Simpson
• Logan
• Harmon
• Kenna

}}

| extra7 = {{flat list|

• Timbaland
• Logan
• Harmon
• Beanz{{ref|a|[a]}}

}}

| length7 = 4:10

| title8 = What I've Become

| writer8 = {{flat list|

• Simpson
• Kenna
• Logan
• Harmon
• Beanz

}}

| extra8 = {{flat list|

• Timbaland
• Logan
• Harmon
• Beanz{{ref|a|[a]}}
• Demacio "Demo" Castellon{{ref|b|[b]}}

}}

| length8 = 3:51

| title9 = Hot Stuff

| writer9 = {{flat list|

• Simpson
• Hugo
• Kenna
• Beanz

}}

| extra9 = {{flat list|

• Hugo
• Kenna

}}

| length9 = 3:13

| title10 = Murder

| writer10 = {{flat list|

• Simpson
• Logan
• Harmon
• Beanz

}}

| extra10 = {{flat list|

• Timbaland
• Logan
• Harmon
• Beanz{{ref|a|[a]}}

}}

| length10 = 4:02

| title11 = Never Dream Alone

| writer11 = {{flat list|

• Simpson
• Kenna

}}

| extra11 = {{flat list|

• Kenna
• Simpson
• Harmon{{ref|b|[b]}}

}}

| length11 = 3:19

}}

{{Track listing

| headline = Bittersweet World{{nobold| — FYE edition (bonus track)}}

| total_length =

| title12 = Can't Have It All

| length12 = 3:53

}}

{{Track listing

| headline = Bittersweet World{{nobold| — Walmart edition (bonus download)}}

| total_length =

| title12 = I’m Out

| length12 = 3:48

}}

{{Track listing

| headline = Bittersweet World{{nobold| — iTunes Store edition (bonus track)}}

| total_length = 43:29

| title12 = Follow You Wherever You Go

| writer12 = {{flat list|

• Simpson
• Hugo
• Kenna
• Beanz

}}

| length12 = 3:34

}}

{{Track listing

| extra_column = Producer(s)

| headline = Bittersweet World{{nobold| — International edition (bonus track)}}

| total_length = 43:40

| title12 = Invisible

| writer12 = {{flat list|

• Kira Leyden
• Jeff Andrea

}}

| extra12 = {{flat list|

• Ron Fair
• Tal Herzberg{{ref|c|[c]}}

}}

| length12 = 3:45

}}

{{Track listing

| extra_column = Producer(s)

| headline = Bittersweet World{{nobold| — Japanese edition (bonus content)}}

| total_length = 53:36

| title13 = Outta My Head (Ay Ya Ya)

| note13 = DJ AM / Eli Escobar Remix

| writer13 = {{flat list|

• Simpson
• Logan
• Harmon
• White
• Kenna

}}

| extra13 = {{flat list|

• Timbaland
• Logan
• Harmon
• Beanz{{ref|a|[a]}}

}}

| length13 = 6:08

| title14 = Outta My Head (Ay Ya Ya)

| note14 = music video

| writer14 = {{flat list|

• Simpson
• Logan
• Harmon
• White
• Kenna

}}

| extra14 = {{flat list|

• Timbaland
• Logan
• Harmon
• Beanz{{ref|a|[a]}}

}}

| length14 = 3:48

}}

{{Track listing

| extra_column = Producer(s)

| headline = Bittersweet World{{nobold| — European edition (bonus tracks)}}

| total_length = 50:16

| title13 = Pieces of Me

| writer13 = {{flat list|

• Simpson
• Kara DioGuardi
• John Shanks

}}

| extra13 = Shanks

| length13 = 3:37

| title14 = Boyfriend

| writer14 = {{flat list|

• Simpson
• DioGuardi
• Shanks

}}

| extra14 = Shanks

| length14 = 2:59

}}

{{Track listing

| extra_column = Producer(s)

| headline = Bittersweet World{{nobold| — European digital edition (bonus tracks)}}

| total_length = 64:26

| title15 = Outta My Head (Ay Ya Ya)

| note15 = Dave Audé Club Dub

| writer15 = {{flat list|

• Simpson
• Logan
• Harmon
• White
• Kenna

}}

| extra15 = {{flat list|

• Timbaland
• Logan
• Harmon
• Beanz{{ref|a|[a]}}

}}

| length15 = 7:05

| title16 = Outta My Head (Ay Ya Ya)

| note16 = Dave Audé Dub Instrumental

| writer16 = {{flat list|

• Simpson
• Logan
• Harmon
• White
• Kenna

}}

| extra16 = {{flat list|

• Timbaland
• Logan
• Harmon
• Beanz{{ref|a|[a]}}

}}

| length16 = 7:05

}}

;Notes{{cite AV media notes |title=Bittersweet World |others=Ashlee Simpson |year=2008 |type=booklet |publisher=Geffen Records, a division of Universal Music Group |location=Santa Monica, CA}}

• ^{{note|a|a}} signifies a vocal producer
• ^{{note|b|b}} signifies an additional producer
• ^{{note|c|c}} signifies a co-producer
• "Little Miss Obsessive" features guest vocals from Tom Higginson of the Plain White T's.
• "Murder" features a rap from Izza Kizza.

{{Reflist|30em}}

• {{Metacritic album}}

{{Ashlee Simpson}}

{{Authority control}}

Category:2008 albums

Category:Albums produced by Chad Hugo

Category:Albums produced by Jerome "J-Roc" Harmon

Category:Albums produced by Kenna

Category:Albums produced by Timbaland

Category:Ashlee Simpson albums

Category:Geffen Records albums