| Question | Diff. | By | Answers |
| Who lost a bet to Jay and got the task of carrying fake merchandise after Jay has presented them: | Easy | In_Correct | • Andrew • Cindy • Joey • JunkDrawer |
| Who cowrote the monologue until 2001: | Medium | In_Correct | • Jimmy Brogan • Kevin Eubanks • In_Correct • John Melendez |
| Jay Leno traded places for one day with: | Medium | In_Correct | • Katie Couric • David Letterman • Ben21 • Tom Brokaw |
| Who was The Tonight Show with Jay Leno's first guest in 1992: | Hard | In_Correct | • Billy Crystal • Barbara Streisand • Bette Midler • Sebrioth |
| What year did Branford Marsalis leave the show: | Easy | In_Correct | • 1992 • 1995 • 2009 • 2010 |
| What Year did Branford Marsalis begin on the show: | Easy | In_Correct | • 1992 • 1995 • 2009 • 2010 |
| What year did Kevin Eubanks leave the show: | Medium | In_Correct | • 1992 • 1995 • 2009 • 2010 |
| What year did Kevin Eubanks begin on the show: | Easy | In_Correct | • 1992 • 1995 • 2009 • 2010 |
| The segment where he reads typos in newspapers is called: | Easy | In_Correct | • Typos • Headlines • Errors • Articles |
| When did Jay Leno return to The Tonight Show: | Medium | In_Correct | • September 27, 1954 • May 25, 1992 • April 26, 1999 • March 01, 2010 |
| When did Jay Leno begin hosting The Tonight Show: | Medium | In_Correct | • September 27, 1954 • May 25, 1992 • April 26, 1999 • March 01, 2010 |
| When did The Tonight Show with Jay Leno first broadcast in High Definition | Medium | In_Correct | • September 27, 1954 • May 25, 1992 • April 26, 1999 • March 01, 2010 |