Host with the Most

Jay Leno’s career is storied and star-studded. Here are some highlights—and a few low points—in the life of the king of late-night TV.

1993

Leno broadcasts The Tonight Show live from the bar in Boston where Cheers commemorates its final episode. The idea flops as the cast gets sloppy drunk!

1994

Leno receives a little “heat” from Bobcat Goldthwait, (the guy with the irritating voice from all those Police Academy films) who appears as a guest and deliberately sets his chair on fire!

1995

Leno finally beats CBS rival David Letterman by asking Hugh Grant—who’d just been arrested for soliciting a prostitute—“What were you thinking?” Grant replied, “I think you know in life what’s a good thing to do and what’s a bad thing, and I did a bad thing. And there you have it.” And there you have it—the simplest public apology ever.

2003

After manning the hot seat for 17 years, Leno does the unthinkable: he swaps spots with Katie Couric trading tonight for Today. Couric interviews guests Mike Myers and Simon Cowell, while Leno chats with the crowd after thrilling them with his stunt driving.

2005

After testifying in Michael Jackson’s child-molestation trial, Leno is prohibited from mentioning the Gloved One in his monologue. Exploiting a loophole, Leno has guest comedians Brad Garrett and Roseanne Barr tell his jokes about the pop-star defendant in his place.

2006

Leno has two very special guests on his couch—hunky actor Colin Farrell and Farrell’s “very first” stalker, Dessarae Bradford. Bradford leaves her seat during the show’s taping to confront Farrell for failing to show up for their “sex date.” Leno has her removed from the set.

2008

Even though the Writers Guild is still on strike, The Tonight Show must go on! Returning to air, Republican presidential candidate Mike Huckabee appears as a guest on the show—leaving audiences wishing the strike was over.

2009

President Barack Obama spends some time on Jay’s couch, making him the first sitting president to appear on a late night talk show—with a record number of undercover Secret Service agents in the audience.