Year |
Actor |
Program |
Role |
Episode(s) |
Network |
1999–2000 (52nd) |
Sean Hayes |
Will & Grace |
Jack McFarland |
"Homo for the Holidays" + "Acting Out" |
NBC |
Peter Boyle |
Everybody Loves Raymond |
Frank Barone |
"Prodigal Son" + "Debra Makes Something Good" |
CBS |
Brad Garrett |
Robert Barone |
"Someone's Cranky" + "Confronting the Attacker" |
Peter MacNicol |
Ally McBeal |
John Cage |
N/A |
Fox |
David Hyde Pierce |
Frasier |
Dr. Niles Crane |
"Rivals" + "A Tsar Is Born" |
NBC |
2000–2001 (53rd) |
Peter MacNicol |
Ally McBeal |
John Cage |
"Reasons to Believe" + "In Search of Barry White" |
Fox |
Peter Boyle |
Everybody Loves Raymond |
Frank Barone |
"The Wallpaper" + "Frank Paints the House" |
CBS |
Robert Downey Jr. |
Ally McBeal |
Larry Paul |
"Sex, Lies, and Second Thoughts" + "The Obstacle Course" |
Fox |
Sean Hayes |
Will & Grace |
Jack McFarland |
"Grace 0, Jack 2000" + "Gypsies, Tramps and Weed" |
NBC |
David Hyde Pierce |
Frasier |
Dr. Niles Crane |
"Hooping Cranes" + "Daphne Returns" |
2001–2002 (54th) |
Brad Garrett |
Everybody Loves Raymond |
Robert Barone |
"Lucky Suit" + "Raybert" |
CBS |
Peter Boyle |
Everybody Loves Raymond |
Frank Barone |
"Frank Goes Downstairs" + "The Kicker" |
CBS |
Bryan Cranston |
Malcolm in the Middle |
Hal |
"Poker" + "Money" |
Fox |
Sean Hayes |
Will & Grace |
Jack McFarland |
"A Chorus Lie" + "Went to a Garden Potty" |
NBC |
David Hyde Pierce |
Frasier |
Dr. Niles Crane |
"Room Full of Heroes" + "Deathtrap" |
2002–2003 (55th) |
Brad Garrett |
Everybody Loves Raymond |
Robert Barone |
"Just a Formality" + "Robert's Wedding" |
CBS |
Peter Boyle |
Everybody Loves Raymond |
Frank Barone |
"Grandpa Steals" + "Meeting the Parents" |
CBS |
Bryan Cranston |
Malcolm in the Middle |
Hal |
"Malcolm Holds His Tongue" + "Day Care" |
Fox |
Sean Hayes |
Will & Grace |
Jack McFarland |
"Bacon & Eggs" + "The Needle and the Omelets Done" |
NBC |
John Mahoney |
Frasier |
Martin Crane |
"The Devil and Dr. Phil" + "Fathers and Sons" |
David Hyde Pierce |
Dr. Niles Crane |
"Fraternal Schwinns" + "Roe to Perdition" |
2003–2004 (56th) |
David Hyde Pierce |
Frasier |
Dr. Niles Crane |
"No Sex Please, We're Skittish" + "Goodnight, Seattle" (Part 2) |
NBC |
Peter Boyle |
Everybody Loves Raymond |
Frank Barone |
"Jazz Records" + "The Mentor" |
CBS |
Brad Garrett |
Robert Barone |
"The Model" + "Golf for It" |
Sean Hayes |
Will & Grace |
Jack McFarland |
"Me and Mr. Jones" + "I Never Cheered for My Father" |
NBC |
Jeffrey Tambor |
Arrested Development |
George and Oscar Bluth |
"Visiting Ours" + "Not Without My Daughter" |
Fox |
2004–2005 (57th) |
Brad Garrett |
Everybody Loves Raymond |
Robert Barone |
"A Job for Robert" + "Pat's Secret" |
CBS |
Peter Boyle |
Everybody Loves Raymond |
Frank Barone |
"Boys' Therapy" + "Tasteless Frank" |
CBS |
Sean Hayes |
Will & Grace |
Jack McFarland |
"Queens for a Day" + "It's a Dad, Dad, Dad, Dad World" |
NBC |
Jeremy Piven |
Entourage |
Ari Gold |
"The Review" + "Busey and the Beach" |
HBO |
Jeffrey Tambor |
Arrested Development |
George and Oscar Bluth |
"Burning Love" + "The Righteous Brothers" |
Fox |
2005–2006 (58th) |
Jeremy Piven |
Entourage |
Ari Gold |
"The Bat Mitzvah" + "Exodus" |
HBO |
Will Arnett |
Arrested Development |
George "Gob" Bluth II |
"Making a Stand" + "S.O.B.s" |
Fox |
Bryan Cranston |
Malcolm in the Middle |
Hal |
"College Recruits" + "Hal Grieves" |
Jon Cryer |
Two and a Half Men |
Dr. Alan Harper |
"Weekend in Bangkok with Two Olympic Gymnasts" + "Ergo, the Booty Call" |
CBS |
Sean Hayes |
Will & Grace |
Jack McFarland |
"Alive and Schticking" + "I Love L. Gay" |
NBC |
2006–2007 (59th) |
Jeremy Piven |
Entourage |
Ari Gold |
"Manic Monday" |
HBO |
Jon Cryer |
Two and a Half Men |
Dr. Alan Harper |
"Repeated Blows to His Unformed Head" |
CBS |
Kevin Dillon |
Entourage |
Johnny "Drama" Chase |
"The Resurrection" |
HBO |
Neil Patrick Harris |
How I Met Your Mother |
Barney Stinson |
"Showdown" |
CBS |
Rainn Wilson |
The Office |
Dwight Schrute |
"The Coup" |
NBC |
2007–2008 (60th) |
Jeremy Piven |
Entourage |
Ari Gold |
"The Day Fuckers" |
HBO |
Jon Cryer |
Two and a Half Men |
Dr. Alan Harper |
"Meander to Your Dander" |
CBS |
Kevin Dillon |
Entourage |
Johnny "Drama" Chase |
"The Dream Team" |
HBO |
Neil Patrick Harris |
How I Met Your Mother |
Barney Stinson |
"The Goat" |
CBS |
Rainn Wilson |
The Office |
Dwight Schrute |
"Money" |
NBC |
2008–2009 (61st) |
Jon Cryer |
Two and a Half Men |
Dr. Alan Harper |
"Sir Lancelot's Litter Box" |
CBS |
Kevin Dillon |
Entourage |
Johnny "Drama" Chase |
"Tree Trippers" |
HBO |
Neil Patrick Harris |
How I Met Your Mother |
Barney Stinson |
"Benefits" |
CBS |
Jack McBrayer |
30 Rock |
Kenneth Parcell |
"The Bubble" |
NBC |
Tracy Morgan |
Tracy Jordan |
"The Funcooker" |
Rainn Wilson |
The Office |
Dwight Schrute |
"Heavy Competition" |