Leno’s ‘Tonight Show’ Top 10

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  • Leno Mono AP 1992

    Jay Leno gestures during the opening monologue at the inauguration of "The Tonight Show with Jay Leno" which was broadcast live on the east coast from NBC Studios in Burbank, Calif., May 25, 1992. The show features a new band with jazz musician Branford Marsalis as musical director. Leno's first guests were comedian Billy Crystal and singer Shanice. (AP Photo/Craig Fujii)

    Jay Leno’s Top 10 ‘Tonight Show’ moments

    Jay Leno will be on stage Friday in front of a capacity crowd at the Van Wezel Performing Arts Hall in Sarasota, a mere day after leaving, for the second time, “The Tonight Show.” Leno, who has ruled the late night ratings wars for most of his career, leaves behind one of the greatest legacies in the history of television. To commemorate the 63-year-old’s amazing run, we are borrowing a bit from the playbook of his former nemesis David Letterman. Here’s a “Top Ten,” in chronological order, of the defining moments of “The Tonight Show with Jay Leno.”

  • Leno Crystal AP 1992

    AP Photo/Craig Fujii

    1. Billy Crystal sings hello (May, 1992)

    Billy Crystal, the first guest on “The Tonight Show with Jay Leno,” looks into the eyes of the host and croons the hilarious “Dear Mr. Leno.” No word as of this morning on what Crystal might sing when he appears as Leno’s final guest.

  • Leno Cheers AP 1993

    AP Photo/Charles Krupa

    2. “Cheers” cast drunk (May, 1993)

    Leno does a live show from Boston's Bull and Finch pub the night "Cheers" goes off the air and pretty much the whole cast of the sitcom is totally hammered. Good times!

  • Leno Hugh Grant AP 1995

    AP Photo/Eric Draper

    3. Hugh Grant humiliated (July, 1995)

    Hugh Grant, the handsome British actor dating hottie Elizabeth Hurley, chooses "The Tonight Show” to make his first public appearance after his arrest involving a prostitute. Leno asks the perfect, no-brainer: “What the hell were you thinking?”

  • Leno Gibson AP 1997

    AP Photo/Damian Dovarganes

    4. Passion of the Gibson (May, 1997)

    Mel Gibson goes all Roman soldier on Leno and sneak slams the host in the face with a cake to celebrate Leno’s fifth year at the helm of "The Tonight Show." In 2012, Gibson would surprise absolutely no one by telling Leno he’s got “a little bit of a temper.”

  • Leno Arnold AP 2003

    AP Photo/Kevork Djansezian

    5. The Governator (August, 2003)

    Arnold Schwarzenegger isn’t joking with Leno when he announces he will run for governor of California. In a twist less believable than the plots of his movies, Schwarzenegger wins

  • Leno Michale Jackson Roseanne AP 2005 CROP

    AP Photo/NBC Universal, Margaret Norton

    6. Last laugh with Michael Jackson jokes (March, 2005)

    Leno, subpoenaed for Michael Jackson's trial and barred from discussing it outside court, gets the last laugh. Smirking but silent, he stands by while celebrity guests such as Roseanne Barr deliver Jackson jokes during the monologue.

  • Leno Obama AP 2009

    AP Photo/Gerald Herbert

    7. Dear Mr. President (March, 2009)

    President Barack Obama charms Leno and a slim majority of his viewers while becoming the first sitting president to be a guest on “The Tonight Show.” The New York Times extols the president’s performance, calling it “a fireside chat for the flat screen age.”

  • Leno Conan AP 2009

    AP Photo/NBC, Paul Drinkwater

    8. First final taping, with Conan (May, 2009)

    Conan O'Brien is interviewed by Leno during Leno's final taping as host of “The Tonight Show.” You know, because O'Brien is taking over.

  • Leno returns AP 2010

    AP Photo/Damian Dovarganes

    9. Leno returns (March, 2010)

    “The Jay Leno Show” ends after a short run in February of 2010 and next month O’Brien is out and Leno is back as host of "The Tonight Show." Many people, especially comedians, will never forgive Leno for this move.

  • Leno Fallon AP 2013

    AP Photo/NBC, Paul Drinkwater

    10. Fallon to replace Leno (April, 2013)

    NBC announces in April that Jimmy Fallon will succeed Leno as the host of “The Tonight Show” following the 2014 Winter Olympics. Fallon and Leno appear together during the Golden Globe Awards in January and Fallon whispers: “Please, Jay, don’t Conan O’Brien me.”