| Year | Image | Recipient | Notes |
| 1998 (1st) | | Richard Pryor | Those there to honor Pryor included Chris Rock, Robin Williams, Whoopi Goldberg, Chevy Chase, Tim Allen, Danny Glover, Damon Wayans, Kris Kristofferson, Richard Belzer, Morgan Freeman, Ruth Brown and Dick Gregory; Gene Wilder appeared in a pre-taped video. |
| 1999 (2nd) | | Jonathan Winters | Those there to honor Winters included Steve Allen, Sid Caesar, Robin Williams, Bonnie Hunt, Robert Wuhl, Eugene Levy and Michael McKean. |
| 2000 (3rd) | | Carl Reiner | Those there to honor Reiner included Steve Martin, Mary Tyler Moore, Dick Van Dyke, Jerry Seinfeld, Rob Reiner, Joy Behar, Richard Belzer, and George Wallace; Mel Brooks and Ray Romano appeared in pre-taped videos. |
| 2001 (4th) | | Whoopi Goldberg | Those there to honor Goldberg included Robin Williams, Billy Crystal, Wanda Sykes, Cedric the Entertainer, Chris Tucker, Alan King, Bruce Valanche, Caroline Rhea, Tommy Davidson and Harry Belafonte. |
| 2002 (5th) | | Bob Newhart | Those there to honor Newhart included Kelsey Grammer, David Hyde Pierce, The Smothers Brothers, Don Rickles, Tim Conway, Bernie Mac, Jane Curtin, Fred Willard, Julia Sweeney and Steven Wright. |
| 2003 (6th) | | Lily Tomlin | Those there to honor Tomlin included Jane Fonda, Robin Williams, Dave Chappelle, Elaine Stritch, Doris Roberts, George Lopez, Darrell Hammond, Catherine O'Hara, Miss Piggy and Dolly Parton; Whoopi Goldberg and Steve Martin appeared in pre-taped videos. |
| 2004 (7th) | | Lorne Michaels | Michaels, a Canadian-American, is the only recipient as of 2025[update] born and raised outside of the United States. Those who honored Michaels included Steve Martin, Dan Aykroyd, Tina Fey, Maya Rudolph, Tim Meadows, David Spade, Paul Simon, Conan O'Brien, Christopher Walken, Senator John McCain, and Amy Poehler. |
| 2005 (8th) | | Steve Martin | Those who honored Martin included Tom Hanks, Martin Short, Larry David, Dave Barry, Eric Idle, Diane Keaton, Claire Danes, Queen Latifah, Randy Newman, Paul Simon, Mike Nichols. |
| 2006 (9th) | | Neil Simon | Those there to honor Simon included Nathan Lane, Matthew Broderick, Jason Alexander, Robert Klein, Paul Reiser, Christina Applegate, Richard Dreyfus, and Robert Redford. |
| 2007 (10th) | | Billy Crystal | Those who honored Crystal included Robin Williams, Whoopi Goldberg, Robert De Niro, Danny DeVito, Jimmy Fallon, Jon Lovitz, Martin Short, Rob Reiner, Bob Costas, Barbara Walters, and John Goodman. |
| 2008 (11th) | | George Carlin | The award is not intended to be given posthumously, but Carlin's death occurred between the announcement and the ceremony. Those there to honor Carlin included Joan Rivers, Jon Stewart, Bill Maher, Lewis Black, Denis Leary, Margaret Cho, Garry Shandling, and Lily Tomlin. |
| 2009 (12th) | | Bill Cosby | Those who honored Cosby included Jerry Seinfeld, Chris Rock, Sinbad, Malcolm-Jamal Warner, Steven Wright, Willie Nelson, Carl Reiner, Dick Gregory, Rita Moreno, and Phylicia Rashad.(Cosby's award was rescinded in 2018 due to a sexual assault conviction.) |
| 2010 (13th) | | Tina Fey | Those who honored Fey included Alec Baldwin, Amy Poehler, Steve Martin, Steve Carell, Jimmy Fallon, Jon Hamm, Fred Armisen, Seth Meyers, Jennifer Hudson, Betty White, Jane Krakowski, and Lorne Michaels. |
| 2011 (14th) | | Will Ferrell | Those who honored Ferrell included Conan O'Brien, John C. Reilly, Ben Stiller, Jack Black, Paul Rudd, Adam McKay, Tim Meadows, Matthew Broderick, and Ed Asner. |
| 2012 (15th) | | Ellen DeGeneres | Those there to honor DeGeneres included Jane Lynch, Sean Hayes, Jimmy Kimmel, John Leguizamo, John Krasinski, Steve Harvey, Kristin Chenoweth, and Lily Tomlin. |
| 2013 (16th) | | Carol Burnett | Those there to honor Burnett included Julie Andrews, Tina Fey, Amy Poehler, Maya Rudolph, Rashida Jones, Martin Short, Tony Bennett, Vicki Lawrence, and Tim Conway; Carl Reiner and Ellen DeGeneres appeared in pre-taped videos. |
| 2014 (17th) | | Jay Leno | Those there to honor Leno included Jerry Seinfeld, Jimmy Fallon, Seth Meyers, Robert Klein, J.B. Smoove, Jamie Foxx, Wanda Sykes, Chelsea Handler, Kristin Chenoweth, and Garth Brooks. |
| 2015 (18th) | | Eddie Murphy | Those there to honor Murphy included Dave Chappelle, Chris Rock, Arsenio Hall, Jay Pharoah, Tracy Morgan, Trevor Noah, George Lopez, Kevin Nealon, and Kathy Griffin. |
| 2016 (19th) | | Bill Murray | Those who honored Murray included David Letterman, Emma Stone, Bill Hader, Aziz Ansari, Miley Cyrus, Jane Curtin, Jimmy Kimmel, Brian Doyle Murray, and Sigourney Weaver. |
| 2017 (20th) | | David Letterman | Those there to honor Letterman included Bill Murray, Steve Martin, Martin Short, John Mulaney, Norm Macdonald, Jimmy Kimmel, Jimmie Walker, and Eddie Vedder; Michelle Obama appeared in a pre-taped video. Al Franken appeared but was cut from the broadcast due to sexual harassment allegations against him. |
| 2018 (21st) | | Julia Louis-Dreyfus | Those there to honor Louis-Dreyfus included Jerry Seinfeld, Tina Fey, Stephen Colbert, Bryan Cranston, Tony Hale, Lisa Kudrow, Keegan-Michael Key, Kumail Nanjiani, Abbi Jacobson, Ilana Glazer, and Jack Johnson; Larry David appeared in a pre-taped video. |
| 2019 (22nd) | | Dave Chappelle | Those who honored Chappelle included Q-Tip, Jon Stewart, Bradley Cooper, Morgan Freeman, Aziz Ansari, Lorne Michaels, Mos Def, Talib Kweli, Erykah Badu, Sarah Silverman, Neal Brennan, Kenan Thompson, Michael Che, Colin Jost, Chris Tucker, Tiffany Haddish, Common, John Legend, and Chrissy Teigen. Eddie Murphy appeared in a pre-taped video. The PBS broadcast of the ceremony was unique, because footage of the ceremony was interspersed with footage of Chappelle performing standup in a comedy club. |
| 2022 (23rd) | | Jon Stewart | Those who honored Stewart included Samantha Bee, Steve Carell, Dave Chappelle, Pete Davidson, Ed Helms, Jimmy Kimmel, Jon Meacham, Olivia Munn, Bassem Youssef, and Bruce Springsteen. Stephen Colbert appeared remotely via video chat and John Oliver appeared in a pre-taped video that satirized a eulogy. |
| 2023 (24th) | | Adam Sandler | Those who honored Sandler included Dana Carvey, Luis Guzmán, Tim Herlihy, Idina Menzel, Rob Schneider, Ben Stiller, Jennifer Aniston, Judd Apatow, Drew Barrymore, Steve Buscemi, Conan O'Brien, Chris Rock, Pete Davidson, and David Spade. |
| 2024 (25th) | | Kevin Hart | Those who honored Hart include Jerry Seinfeld, Dave Chappelle, Chris Rock, Jimmy Fallon, J.B. Smoove, Tiffany Haddish, Regina Hall, Chelsea Handler, Nick Cannon and Keith Robinson. |
| 2025 (26th) | | Conan O'Brien | Those who honored O'Brien include David Letterman, Will Ferrell, Adam Sandler, John Mulaney, Sarah Silverman, Andy Richter, Stephen Colbert, Bill Burr, Nikki Glaser, Sean Evans, Tracy Morgan, Kumail Nanjiani, and Reggie Watts. Martin Short, Bill Hader, Paul Rudd and Fred Armisen all appeared in pre-taped videos. The Interrupter, Triumph the Insult Comic Dog, the FedEx Pope, the Masturbating Bear, and Jordan Schlansky all briefly appear to hand off the Prize to Letterman who presents it to O'Brien. Will Forte portrayed Mark Twain. |
