1 HUGH GRANT IS SORRY (JULY 10, 1995)
After his highly publicized arrest for being caught with a prostitute, the British actor makes his first public appearance on the show, and Leno famously asks, ”What the hell were you thinking?” The buzzworthy episode cements his ratings hold over David Letterman.
2 BARACK OBAMA INTERVIEW (MARCH 19, 2009)
Obama becomes the first sitting president to appear on a late-night talk show, but causes a small stir when he compares his bowling skills to something out of the Special Olympics.
3 BOBCAT GOLDTHWAIT GETS FIRED UP (MAY 6, 1994)
The antic comedian ignites the guest chair, later claiming that he was avenging the cancellation of The Arsenio Hall Show.
4 THE DANCING ITOS (MARCH 2, 1995)
Leno found endless fodder in the O.J. Simpson trial, eventually turning it into a recurring musical number with a kick line of Judge Lance Itos.
5 ARNOLD SCHWARZENEGGER ANNOUNCES CANDIDACY (AUG. 6, 2003)
Arnold bypasses the traditional press corps and uses Tonight to announce he’ll run for governor of California. Even his advisers, who thought he was staying out of the race, are surprised.
6 CHEERS SAYS CHEERS! (MAY 20, 1993)
Leno takes his show to Boston, where the raucous cast members of Cheers are celebrating the series finale — and most are far too drunk to realize they’re actually appearing live.
7 ANGIE HARMON SAYS YES (MARCH 13, 2000)
The Law & Order star thinks she’s chatting with Leno to talk up her show until her boyfriend, the New York Giants’ Jason Sehorn, surprises her with a marriage proposal.
8 THE JOKE’S ON JACKO (MARCH 4-10, 2005)
Leno — forbidden to make fun of Michael Jackson since being called as a witness in his child-molestation trial — invites comedians Roseanne, Dennis Miller, and others to sub in and tell the jokes for him.
9 KATIE COURIC AND JAY LENO SWITCH JOBS (MAY 12, 2003)
Leno kicks it with Matt Lauer early morning in New York, and Couric stays up way past her bedtime to see how the late-night hosts live.
10 PAUL NEWMAN GOES FAST AND FURIOUS (APRIL 8, 2005)
The actor and racing enthusiast takes on Leno in the Indy 500 of go-cart races, handily winning a loop around the soundstages. It’s one of the car-crazy host’s favorite episodes.