| Dates | Hint | Answer | % Correct |
|---|---|---|---|
| 1997-2005 | Started his own show immediately following the Daily Show | Stephen Colbert | 85%
|
| 2006-2013 | Guest Host and Senior British Person | John Oliver | 77%
|
| 1999-2005 | Became well-known later as Michael Scott | Steve Carell | 77%
|
| 2002-2006 | Lost a tooth in The Hangover | Ed Helms | 73%
|
| 7/03-present | Longest serving correspondent | Samantha Bee | 73%
|
| 9/05-present | Married to the longest serving correspondent | Jason Jones | 62%
|
| 7/96-present | AC/DC | Lewis Black | 62%
|
| 3/14-present | Senior Caucasian Correspondent | Jordan Klepper | 50%
|
| 8/06-present | Senior Black Correspondent | Larry Wilmore | 50%
|
| 2006-2008 | Senior Military Affairs Correspondent | Rob Riggle | 46%
|
| 1/12-present | Senior Beyonce Correspondent | Jessica Williams | 42%
|
| 1999-present | Hoset | Jon Stewart | 42%
|
| 8/06-present | Senior Middle East Correspondent | Aasif Mandvi | 38%
|
| 1996-1998 | Host | Craig Kilborn | 38%
|
| 5/11-present | Senior Latino Correspondent | Al Madrigal | 35%
|
| 6/14-present | Correspondent | Michael Che | 35%
|
| 2010-2011 | Senior Asian Correspondent | Olivia Munn | 35%
|
| 2002-2006 | This Week in God | Rob Corddry | 35%
|
| 2009-2011 | The voice of Olaf | Josh Gad | 31%
|
| 1998-2003 | "Wait, Wait…. Don't Tell Me!" | Mo Rocca | 31%
|
| 2008-2012 | Provided the voice for the Michael Steele puppet | Wyatt Cenac | 31%
|
| 3/08-present | Womens Issues Correspondent | Kristen Schaal | 23%
|
| 1999-2002 | Former SNL member and married to another former TDS cast member | Nancy Walls | 23%
|
| 2005-2006 | Younger brother of another correspondent | Nate Corddry | 23%
|
| 1999-2001 | Has a much more famous little sister | Vance DeGeneres | 23%
|
| 1996-1998 | Former SNL member | A. Whitney Brown | 19%
|
| 1996-1997 | NY Friars' Club Roastmaster General | Jeffrey Ross | 19%
|
| 1996-2000 | Cascade's Kitchen Counselor | Beth Littleford | 15%
|
| 1996-2003 | Out at the Movies | Frank DeCaro | 15%
|
| 1/06-present | A lot of Areas of Expertise, but isn't a Mac | John Hodgman | 15%
|
| 1996-1999 | Public Excess | Rich Brown | 15%
|
| 1998-2003 | "Known to some as ""Fox News reporter"" Trisha Thoon" | Stacey Grenrock-Woods | 15%
|
| 1996 | Susie Greene on Curb Your Enthusiasm | Susie Essman | 15%
|
| 1996-1998 | Will sell you a diesel BMW that won't "Backfire" | Brian Unger | 12%
|
| 2001 | Dollars and Cents | Campbell Smith | 12%
|
| 1999-2002 | The Ugly American | Dave Attell | 12%
|
| 2006 | Poll Smoking | Dave Gorman | 12%
|
| 1996 | Directed "Wet Hot American Summer" | David Wain | 12%
|
| 2005-2008 | Spotted trends | Demetri Martin | 12%
|
| 1996-1997 | Co-created TDS and Co-founded Air America Radio | Lizz Winstead | 12%
|
| 2001-2002 | Mike McLintock on Veep | Matt Walsh | 12%
|
| 1996 | Has Issues along with Michael Ian Black | Michael Showalter | 12%
|
| 2012 | Senior Replacement Correspondent | Patrick Stewart | 12%
|
| 2000-2001 | Lord Viper Scorpion | Tom Johnson | 12%
|
| 1998-2000 | "All Up in That, Elderly Consumer Advocate" | Al Greenwood | 8%
|
| 1998 | Former Good Morning America correspondent | Amy Atkins | 8%
|
| 200-2001 | "TV Guy, voice of Mort on Bob's Burgers" | Andy Kindler | 8%
|
| 2004-2005 | Was actually a real reporter for 10 years | Bob Wiltfong | 8%
|
| 2007 | Senior Historical Perspectivist | Buck Henry | 8%
|
| 2005-2007 | Replaced Correspondent who left for his own show airing 30 minutes later | Dan Bakkedahl | 8%
|
| 1999 | Was a frequent performer on Whose Line Is It Anyway | Denny Siegel | 8%
|
| 1997-1998 | "C'mon, Son!" | Ed Lover | 8%
|
| 1998-1999 | On The Panel | Jeff Stilson | 8%
|
| 1996-1999 | God Stuff | John Bloom | 8%
|
| 2001-2002 | "We Love Showbiz" | Lauren Weedman | 8%
|
| 2002 | Deputy Cherisha Kimball | Mary Birdsong | 8%
|
| 1996-1999 | Ad Nauseam | Michael Blieden | 8%
|
| 2000-2001 | Got her start on Conan | Miriam Tolan | 8%
|
| 1996-1997 | Co hosted movie reviews | Molly Pesce | 8%
|
| 1998 | Us People's Weekly Entertainment | Paul F. Tompkins | 8%
|
| 2002-2003 | Dumped by another former TDS cast member in The Hangover in favor of a stripper | Rachael Harris | 8%
|
| 1997 | Won a Polk Award for his coverage of the US invasion of Panama | Robert Knight | 8%
|
| 1997-1998 | "Director of the documentary ""Becoming Muslim""" | Sameer Butt | 8%
|
| 1998-1999 | This Week in Hate | Tom Shillue | 8%
|
| 1999 | What I'm Sayin | William Stephenson | 8%
|
| 1996 | Hilda Spellman | Caroline Rhea | 4%
|
| 2001 | Stage Manager Bobby | Eric Drysdale | 4%
|