| Host | |
| Alex Trebek | |
| Contestants | |
| see below | |
| Announcer | |
| Johnny Gilbert | |
| Broadcast | |
 | |
| Packager | |
| Sony Pictures Television | |
Contestants[]
- David James Elliott (actor)
- Stephen Collins (actor)
- Thomas Gibson (actor)
- Keith Olbermann (anchorman)
- Robin Roberts (anchorman)
- Bob Costas (commentator and anchorman)
- Dave Foley (actor)
- Kathy Kinney (actress)
- Wallace Langham (actor)
- Greg Germann (actor)
- Jodi Applegate (journalist and co-anchor)
- Scott Hamilton (Olympic figure skater)
- Jeff Greenfield (journalist)
- Star Jones (attorney, correspondent and co-host)
- Al Franken (author and radio talk show host from New York City)
Game Summary[]
| Game | Themed Night | Air Date | Name | Score | Name | Score | Name | Score | Detail |
|---|---|---|---|---|---|---|---|---|---|
| 1 | Leading Men Night | February 5, 1999 | Thomas Gibson | $19,400 | Stephen Collins | $11,000 | David James Elliott | $8,800 | # |
| 2 | Sports Anchors Night | March 22, 1999 | Bob Costas | $20,000 | Robin Roberts | $0 | Keith Olbermann | $5,900 | # |
| 3 | Sitcom Stars Night | March 29, 1999 | Wallace Langham | $16,800 | Kathy Kinney | $12,100 | Dave Foley | $0 | # |
| 4 | TV Personalities Night | April 5, 1999 | Scott Hamilton | $14,400 | Jodi Applegate | $14,401 | Greg Germann | $6,000 | # |
| 5 | Corresponders Night | April 12, 1999 | Al Franken | $15,000 | Star Jones | $3,700 | Jeff Greenfield | $18,000 | # |
Trivia[]
- Al Franken later appeared on 2004 Power Players Week.
List[]
| 1992 | 1993 | 1994 | 1995 | 1996 | 1997 |
| 1998 | 1998-A | 1998-B | 1999 | 1999-A | 1999-B |
| 2001 | 2003 | 2006 | 2009 | 2015 | |
Tournaments
| |||||
| 2009-2010 | 2022-2023 | 2023-2024 | 2025 | ||