| 2025-02-20 | Only character shown in the final 30 minutes of "2001: A Space Odyssey" |
| 2024-11-29 | Half of a noted arcade pair |
| 2024-03-10 | Protagonist in "2001: A Space Odyssey" |
| 2023-03-17 | Rocker Grohl |
| 2023-01-29 | "I'm sorry, ___, I'm afraid I can't do that" (line from HAL in "2001") |
| 2018-04-19 | Singer/songwriter Matthews |
| 2016-08-17 | "Affirmative, ___, I read you" (line in "2001: A Space Odyssey") |
| 2014-05-02 | Actor Franco of "Now You See Me" |
| 2013-12-02 | Letterman of late-night |
| 2013-02-13 | Humorist Barry |
| 2012-11-25 | Thwarter of HAL |
| 2012-06-12 | Humorist Barry |
| 2012-04-18 | Brubeck of jazz |
| 2011-04-02 | Writer Eggers |
| 2010-09-09 | "Late Show" host, colloquially |
| 2009-05-08 | Early TV host Garroway |
| 2007-06-19 | Comic Chappelle |
| 2006-05-13 | Comedian Chappelle |
| 2005-04-18 | Host Letterman |
| 2003-12-10 | Humorist Barry |
| 2003-05-08 | Starsky of "Starsky and Hutch" |
| 2001-11-19 | Pulitzer-winning humorist Barry |
| 2001-10-20 | Noted Barry |
| 2001-10-01 | Letterman of late-night |
| 2001-08-08 | Pianist Brubeck |
| 2001-06-13 | 1993 Kevin Kline movie |
| 2000-12-17 | Singer Matthews |
| 2000-08-29 | 1993 film in which Kevin Kline played the president |
| 1999-10-16 | 1993 Kevin Kline title role |
| 1999-08-24 | Jay's competition |
| 1999-03-28 | Hoopster Hall-of-Famer Bing |
| 1998-12-23 | Late-night name |
| 1998-04-20 | TV's Letterman |
| 1997-08-03 | 1993 Kevin Kline comedy |
| 1997-06-10 | Garroway of early TV |
| 1997-03-05 | "___ Barry Turns 40" (1990 best seller) |
| 1994-03-26 | 1993 Kevin Kline movie |
| 1994-01-13 | Garroway of '50s TV |