Hugh Grant – 1995
The British actor known for playing stammering characters had recently been caught cheating on his longtime girlfriend, actress Elizabeth Hurley, with a prostitute. And Leno — not David Letterman or Oprah or even Ted Koppel — asked Grant the question on everyone’s minds: “What the hell were you thinking?”
The O.J. Trial & Dancing Itos – 1995
Leno got a ton of mileage out of the “Trial Out of the Century.” The Dancing Itos — five dancing versions of the judge presiding over O.J. Simpson’s trial, Lance Ito — made their debut in March 1995.
Go-Karting with Paul Newman – 2005
Oscar winner and food impresario Paul Newman visited the “Tonight Show” in 2005 to talk cars with auto enthusiast Leno. Of course, the host couldn’t pass up the opportunity to challenge Newman — a long-time racing buff — to a go-kart race around the studio.
President Obama – 2009
Leno landed the first ever interview with a sitting president on a late-night talk show when President Obama visited in March 2009, just a few weeks into Obama’s first term. Obama has been on the “Tonight Show” twice since, as well as “Late Night With Jimmy Fallon” and rival “Late Show With David Letterman” on CBS.
Also read: Jay Leno on ‘Tonight Show’ Exit: 5 Other Surprising Quotes From His ’60 Minutes’ Interview (Video)
Best of Jaywalking – 2009
Back in May 2009, when Leno had his first “Tonight Show” final bow, the host put together a highlight reel with some of his favorite interviewees on “Jaywalking,” the timeless segment that highlights the basic street knowledge of your neighbors and mine.
Best of Headlines
By the same token, Leno’s weekly “Headlines” segment was always a fan favorite.
Also read: Jay Leno, Julia Louis-Dreyfus Among Television Academy’s Hall of Fame Inductees
Kanye’s Apology – 2009
Not all of Leno’s greatest moments during his nonconsecutive 22-year span as “Tonight Show” host occurred when he was actually the “Tonight Show” host. Who can forget those awkward few months when he had his own 10 p.m. “Jay Leno Show”? Though that series was a flop, it yielded a few nuggets, like this impromptu apology from rapper Kanye West for interrupting Taylor Swift at MTV’s Video Music Awards.
Jimmy Kimmel – 2010
When Leno returned to the “Tonight Show,” he brought rival late show host Jimmy Kimmel on for a 10-questions segment. Little did Leno know the ABC host would take the opportunity to ridicule him over the whole debacle.
Also read: Jay Leno Mocks Dems More Than GOP, New Study Finds
NBC Battles — 2013
By the end of his run on the “Jay Leno Show,” the host was barely concealing his contempt for the NBC’s blunderous decision-making. When rumors that NBC was planning to replace him with Jimmy Fallon at the helm of the “Tonight Show” started circulating in 2013, Leno started throwing regular barbs at network brass, including calling NBC execs “snakes” in one joke.
But, as we now know, Leno has graciously passed the torch to Fallon, who takes the chair when the “Tonight Show” returns on Feb. 17.