A Last Look at Jay Leno on 'The Tonight Show'

By Rebecca Harper, Hulu | Thursday, May 28, 2009, 4:51 PM

Jay Leno moves to primetime in the fall.

NBC/Paul Drinkwater

After 17 years of battling it out with David Letterman for the title of "King of Late Night," Jay Leno steps down as host of "The Tonight Show With Jay Leno" this week, handing the title to successor Conan O'Brien. (His show starts June 1.) Before Leno returns to NBC during primetime in the fall, the Hulu team pulled together some of their favorite moments from Leno's reign on "The Tonight Show," including a tribute to Ross "The Intern" Mathews and a presidential faux pas.

Brad Pitt Will Do Anything

Celebrities know they can always rely on their friend Jay Leno to invite them on "The Tonight Show" to help spread the word about their new movies. But even still, sometimes an actor has to go that extra mile to get people into the theaters opening weekend. Check out the lengths Brad Pitt went to in order to promote his 2001 movie "Spy Game."

Best of Ross the Intern

Ross Mathews' life changed on the last day of his "Tonight Show" internship, when he was sent to the "Ocean's Eleven" premiere with George Clooney. That assignment began his stint as an official correspondent for Leno and, over the following seven and a half years, he caught up with some of the biggest names in the business: Tom Cruise, Oprah, Steven Spielberg, Gwyneth Paltrow and Madonna. Leno pays homage to his former intern with this montage of greatest hits -- through a segment with Crocodile Hunter Steve Irwin, we learn Ross' code word for uncomfortable situations: "pineapple."

Tattoo or No Tattoo

Leno famously appeals to the masses as a comedian who can reach young and old, rich and poor audiences alike. (Of course, NBC is counting on this broad appeal by placing him in the 10pm slot this fall.) Some of his most popular sketches are interviews with Average Joe types. "I enjoy the real people stuff," he said in a recent phone interview. "If you see a fat guy, you make fun of his tie. You see a banker, a Wall Street guy, you nail 'em. If he's a working guy, a blue-collar worker, a janitor or something, you build him up." In this segment, Leno chats with some folks on the street and has the audience guess whether they're tattooed or not, getting some laughs along the way.

Best Celebrity Correspondents

While Leno may have drawing power, he also has plenty of high-profile friends. Over the years, Leno has recruited fellow celebrities to cover special events including movie premieres, the Republican National Convention, even the rodeo. This highlight clip features everyone from Dana Carvey (doing his best Tom Brokaw impression) and Dave Chappelle to Tom Green. Some prize moments: Tom Green on fire, Brian Williams' critique of correspondent Mo Rocca's sweater, and Ryan Seacrest's visit to the rodeo.

Battle of Jaywalk All-Stars

In Leno's "Jaywalking" bits, he quizzes people about all sorts of topics -- American history, geography and current events, to name a few. Here, he hosts a quiz show-style competition to add another name to the Jaywalk Hall of Fame, asking contestants about the inventor of a mysterious device. The answers are astounding.

Anderson Cooper Interview

When roles are reversed and CNN anchor Anderson Cooper finds himself the subject of an interview, he's usually a good sport. In an interview from last fall, the silver-haired journalist opens up to Leno about his guilty pleasure: reality TV shows, specifically "The Real Housewives of Atlanta."

President Obama Interview

President Obama's appearance on "The Tonight Show" in March all but cemented Leno's status as the "King of Late Night." While he and the President casually chatted about adjusting to life in the White House, the current economic climate, and sports, no one could have anticipated the controversy the President would cause with an offhand remark about his bowling skills. He later apologized, but the gaffe called into question the soundness of having the Commander-in-Chief appear on talk shows.

Talk About It: What are some of your favorite "Tonight Show With Jay Leno" moments?