Drama Desk Award for Outstanding Featured Actor in a Musical

! style="width:10%;"| Year

! style="width:30%;"| Actor

! style="width:30%;"| Musical

! style="width:30%;"| Character

| Ted Ross

| The Wiz

| The Lion

| The Wiz

| The Scarecrow

| In Gay Company

| Unknown

| Where's Charley?

| Jack Chesney

| The Night That Made America Famous

| Performer

| Goodtime Charley

| Minguet

| George Rose

| My Fair Lady

| Alfred P. Doolittle

| Pacific Overtures

| Commodore Matthew Calbraith Perry

| Very Good Eddie

| Steward / Al Cleveland

| Bubbling Brown Sugar

| Charlie / Count

| Ken Bichel

| rowspan="4"| I Love My Wife

| Norman

| Michael Mark

| Stanley

| John Miller

| Harvey

| Joseph Saulter

| Quenton

| Music Is

| Feste

| She Loves Me

| Stephen Kodaly

| Music Is

| Malvolio

| Porgy and Bess

| Sportin' Life

| Kevin Kline

| On the Twentieth Century

| Bruce Granit

| Angel

| Ben Gant

| rowspan="2"| Working

| Various Characters

| Mike LeFevre

| Dancin'

| Performer

| The Present Tense

| Performer

| Ken Jennings

| Sweeney Todd

| Tobias Ragg

| Platinum

| Dan Danger

| King of Hearts

| Raoul

! style="width:10%;"| Year

! style="width:30%;"| Actor

! style="width:30%;"| Musical

! style="width:30%;"| Character

| Bob Gunton

| Evita

| Juan Perón

| The 1940's Radio Hour

| Neal Tilden

| Oklahoma!

| Will Parker

| The 1940's Radio Hour

| Johnny Cantone

| Gilda Radner – Live from New York

| Himself

| Oklahoma!

| Jud Fry

| Tony Azito

| The Pirates of Penzance

| The Sergeant of Police

| Sophisticated Ladies

| Performer

| Broadway Follies

| Performer

| 42nd Street

| Billy Lawlor

| Camelot

| Pellinore

| Cleavant Derricks

| Dreamgirls

| James "Thunder" Early

| Pump Boys and Dinettes

| L. M.

| Dreamgirls

| Curtis Taylor, Jr.

| Charles "Honi" Coles

| My One and Only

| Mr. Magix

| Show Boat

| Joe

| Little Shop of Horrors

| Orin Scrivello, D.D.S.

| The Cradle Will Rock

| Larry Foreman

| Martin Vidnovic

| Baby

| Nick Sakarian

| Taking My Turn

| Eric

| The Tap Dance Kid

| Dipsey

| Sunday in the Park with George

| Jules

| René Auberjonois

| Big River

| The Duke

| rowspan="2"|Big River

| Pap Finn

| The King

| La bohème

| Marcel

| Grind

| Doyle

| Big River

| Tom Sawyer

| Michael Rupert

| Sweet Charity

| Oscar Lindquist

| Personals

| Various Characters

| Song and Dance

| Man

| The Mystery of Edwin Drood

| Bazzard / Mr. Philip Bax

| Michael Maguire

| Les Misérables

| Enjolras

| Me and My Girl

| Herbert Parchester

| Smile

| Tommy French

| Gay Divorce

| Teddy

| Robert Westenberg

| Into the Woods

| Cinderella's Prince / The Wolf

| Chess

| Molokov

| rowspan="2"|Anything Goes

| Evelyn Oakleigh

| Moonface Martin

| Dreamgirls

| James "Thunder" Early

| {{n/a}}

| {{n/a}}

| {{n/a}}

! style="width:10%;"| Year

! style="width:30%;"| Actor

! style="width:30%;"| Musical

! style="width:30%;"| Character

| Michael Jeter

| Grand Hotel

| Otto Kringelein

| City of Angels

| Irving S. Irving / Buddy Fidler

| The Sound of Music

| Various Characters

| Gypsy

| Herbie

| Bruce Adler

| Those Were the Days

| Various Characters

| The Secret Garden

| Dickon

| A Funny Thing Happened on the Way to the Forum

| Senex

| Assassins

| Samuel Byck

| Scott Waara

| The Most Happy Fella

| Herman

| Crazy for You

| Bela Zangler

| Guys and Dolls

| Nicely-Nicely Johnson

| Jelly's Last Jam

| Young Jelly

| Mark Michael Hutchinson

| Blood Brothers

| Eddie

| Anna Karenina

| Prince Stephen Oblonsky

| My Favorite Year

| Sy Benson

| Jarrod Emick

| Damn Yankees

| Joe Hardy

| The Red Shoes

| Grisha Ljubov

| Grease

| Doody

| Hello Again

| The Young Thing

| Beauty and the Beast

| Gaston

| {{n/a}}

| {{n/a}}

| {{n/a}}

| Wilson Jermaine Heredia

| Rent

| Angel Dumott Schunard

| rowspan="2"|Swinging on a Star

| Various Characters

| Various Characters

| Big: the musical

| Billy Kopecki

| rowspan="2"|State Fair

| Pat Gilbert

| Wayne Frake

| Joel Grey

| Chicago

| Amos Hart

| When Pigs Fly

| Various Characters

| Play On!

| Jester

| The Life

| Jojo

| Violet

| Flick

| When Pigs Fly

| Various Characters

| Gregg Edelman

| 1776

| Edward Rutledge

| rowspan="2"|The Lion King

| Timon

| Zazu

| High Society

| Uncle Willie

| The Capeman

| Tony Hernandez

| Ragtime

| Mother's younger Brother

| Roger Bart

| You're a Good Man, Charlie Brown

| Snoopy

| Forbidden Broadway Cleans Up Its Act

| Various Characters

| The Civil War

| Clayton Toler

| Parade

| Jim Conley

| It Ain't Nothin' But the Blues

| Various Characters

| A New Brain

| Mr. Bungee

! style="width:10%;"| Year

! style="width:30%;"| Actor

! style="width:30%;"| Musical

! style="width:30%;"| Character

| Stephen Spinella

| James Joyce's The Dead

| Freddy Malins

| Contact

| Husband

| Saturday Night

| Bobby

| Kat and the Kings

| Magoo

| rowspan="2"|Kiss Me, Kate

| Second Man

| First Man

| Gary Beach

| The Producers

| Roger de Bris

| The Producers

| Carmen Ghia

| rowspan="2"|The Full Monty

| Dave Bukatinsky

| Noah "Horse" T. Simmons

| Enter the Guardsman

| The Playwright

| Urinetown

| Officer Lockstock

| Shuler Hensley

| Oklahoma!

| Jud Fry

| Oklahoma!

| Will Parker

| Thou Shalt Not

| Camille Raquin

| Tick, Tick... Boom!

| Michael

| Into the Woods

| Cinderella's Prince / The Wolf

| Thoroughly Modern Millie

| Trevor Graydon III

| Dick Latessa

| Hairspray

| Wilbur Turnblad

| Gypsy

| Herbie

| Amour

| Bertrand

| rowspan="2"|A Man of No Importance

| Carney / Oscar Wilde

| Robbie Fay

| Hairspray

| Seaweed J. Stubbs

| Raúl Esparza

| Taboo

| Phillip Sallon

| Golf: The Musical

| Bob Hope

| Taboo

| Marilyn

| The Boy from Oz

| Boy

| Assassins

| Proprietor

| Wonderful Town

| Wreck

| Denis O'Hare

| Sweet Charity

| Oscar Lindquist

| Spamalot

| Various Characters

| Dirty Rotten Scoundrels

| Andre

| Dessa Rose

| Nathan

| Altar Boyz

| Mark

| Spamalot

| Mayor / Patsy

| Jim Dale

| The Threepenny Opera

| Mr. Peachum

| Sweeney Todd

| The Beadle

| Jersey Boys

| Tommy DeVito

| The Drowsy Chaperone

| George

| Grey Gardens

| J.V. "Major" Bouvier

| Jersey Boys

|Bob Gaudio

| Gavin Lee

| Mary Poppins

| Bert

| Martin Short: Fame Becomes Me

| Comedy All Star

| Legally Blonde

| Emmett Forrest

| Les Misérables

| Enjolras

| Adrift in Macao

| Tempura

| LoveMusik

| Bertolt Brecht

| Boyd Gaines

| Gypsy

| Herbie

| South Pacific

| Luther Billis

| rowspan="2"|Young Frankenstein

|Igor

|The Monster

| The Slug Bearers of Kayrol Island

| Immanuel Lebang

| A Catered Affair

| Tom Hurley

| Gregory Jbara

| Billy Elliot the Musical

| Mr. Elliot

| Happiness

| Stanley

| The Toxic Avenger

| Black Dude

| 9 to 5

| Franklin Hart Jr.

| Hair

| Woof

| Shrek the Musical

|Lord Farquaad

! style="width:10%;"| Year

! style="width:30%;"| Actor

! style="width:30%;"| Musical

! style="width:30%;"| Character

| Christopher Fitzgerald

| Finian's Rainbow

| Og

| The Addams Family

|Uncle Fester

| La Cage aux Folles

| Jacob

| Yank!

| Artie

| Bloodsong of Love

| Lo Cocodrilo

| Ragtime

| Mother's Younger Brother

| John Larroquette

| How to Succeed in Business Without Really Trying

| J.B. Biggley

| Anything Goes

| Lord Evelyn Oakleigh

| Women on the Verge of a Nervous Breakdown

| Ivan

| The Book of Mormon

| Elder McKinley

| Hello Again

| The Husband

| Catch Me If You Can

| Frank Abagnale Sr.

| Michael McGrath

| Nice Work If You Can Get It

| Cookie McGee

| Porgy and Bess

| Crown

| Death Takes a Holiday

| Eric Fenton

| Evita

|Juan Perón

| Spider-Man: Turn Off the Dark

| Green Goblin

| Queen of the Mist

| Frank Russell

| Bertie Carvel

| Matilda the Musical

| Miss Trunchbull

| Passion

| Colonel Ricci

| A Christmas Story: The Musical

| The Old Man

| Hands on a Hardbody

| JD Drew

| Giant

| Bawley

| The Mystery of Edwin Drood

| Neville Landless

| James Monroe Iglehart

| Aladdin

| Genie

| Cabaret

| Herr Schultz

| Bullets Over Broadway: The Musical

| Cheech

| Violet

| Flick

| Nobody Loves You

| Evan

| Big Fish

| William Bloom

| Christian Borle

| Something Rotten!

| The Bard

| Fly By Night

| Mr. McClam

| It Shoulda Been You

| Marty Kaufman

| On the Twentieth Century

| Bruce Granit

| Hamilton

| Aaron Burr

| Something Rotten!

|Nostradamus

| An American in Paris

| Henri Baurel

| Christopher Fitzgerald

| Waitress

| Ogie

| She Loves Me

| Arpad Laszlo

| Disaster!

| Ben / Lisa

| rowspan="2"| Bright Star

| Jimmy Ray Dobbs

| Billy Cane

| Gavin Creel

| Hello, Dolly!

| Cornelius Hackl

| Kid Victory

| Michael

| The Lightning Thief: The Percy Jackson Musical

| Grover

| The Band's Visit

| Haled

| Falsettos

| Mendel

|Gavin Lee

|SpongeBob SquarePants

|Squidward Tentacles

|The Lucky Ones

|Various

|Carousel

|Enoch Snow

|Mean Girls

|Damian Hubbard

|Prince of Broadway

|Various

|André De Shields

|Hadestown

|Hermes

|Kiss Me, Kate

|Bill Calhoun/Lucentio

|Girl from the North Country

|Joe Scott

|Be More Chill

|Michael Mell

|Rodgers & Hammerstein's Oklahoma!

|Jud Fry

! style="width:10%;"| Year

! style="width:30%;"| Actor

! style="width:30%;"| Musical

! style="width:30%;"| Character

| Christian Borle

| Little Shop of Horrors

| Orin Scrivello

| Emojiland

| Nerd Face

| Scotland, PA

| Banko

| Soft Power

| Xue Xing

| The Wrong Man

| The Man in Black

| Matt Doyle

| Company

| Jamie

| Intimate Apparel

| George Armstrong

| Kimberly Akimbo

| Seth

| Funny Girl

| Eddie Ryan

| MJ

| Michael