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    A visual history of Tiger Woods' best (and most painfully awkward) celebrity encounters

    February 14, 2019
    Tiger Jam 2011

    Ethan Miller

    Pro-Ams, Late Night, Tiger Jam, and one unforgettable TRL appearance. Tiger Woods' run-ins with celebrity over the years have been various and hilarious—a snapshot of a kid growing not only into a legend, but also his own jeans. So this week, in honor of Tiger's inaugural Celebrity Cup triumph at the Genesis Open, where he toppled the competition alongside Kid Rock, Mark Wahlberg, Jerry Rice, Larry Fitzgerald, and Paige Spiranac, we decided to a look back at Big Cat's best (and most awkward) celebrity encounters ever. Let's fire up the time machine, shall we?

    Jay Leno - 1996

    The Tonight Show with Jay Leno - Season 5

    NBC

    Say yes to the vest.

    Twister-era Bill Paxton - 1997

    The Tonight Show with Jay Leno - Season 6

    NBC

    Kevin Costner -1997

    AT&T National Pro-Am

    Andy Lyons

    "So what did you think of Tin Cup?"

    The Dream Team -1998

    The Tonight Show with Jay Leno

    NBC

    Kid Rock and Pamela Anderson - 2001

    Tiger Jam IV

    L. Cohen

    Samuel L. Jackson - 2001

    The Ninth Annual ESPY Awards

    Kevin Winter

    Bonding over their shared love of a good f-bomb.

    Carson Daly - 2002

    Tiger Woods Promotes "EA Sports Tiger Woods PGA Tour 2002" Video Game on MTV's "TRL" - March 4, 2002

    KMazur

    Frosted tips and a leather jacket? Who does he think he is? Phil?

    Train - 2002

    Tiger Jam V At Mandalay Bay Events Center In Las Vegas

    Ethan Miller

    Stevie Wonder - 2005

    Tiger Jam VIII - Show

    L. Cohen

    Terri Hatcher and Sam Jackson - 2006

    Tiger Jam IX Benefit Concert - Backstage and Show

    L. Cohen

    Sting - 2006

    Tiger Jam IX Benefit Concert - Arrivals

    L. Cohen

    Terri Hatcher and John Mayer -2007

    Tiger Woods Learning Center Block Party

    Lester Cohen

    Your vertical stripes are a wonderland.

    Mike - 2007

    PGA TOUR - 2007 Wachovia Championship - Pro-Am

    Sam Greenwood

    Will Ferrell - 2007

    Tiger Wood's 10th Annual "Tiger Jam"

    Lester Cohen

    Um, Brick, before I let you go, are you still having your celebrity golf tournament?

    Daughtry - 2007

    Tiger Wood's 10th Annual "Tiger Jam"

    Lester Cohen

    Justin Timberlake - 2008

    2008 ESPY Awards - Show

    Kevin Winter

    Never. Sleeping. Again. #Unchained

    Eddie Van Halen - 2008

    11th Annual Tiger Jam to Benefit the Tiger Woods Foundation - Arrivals

    Lester Cohen

    David Lee Roth- 2008

    USA - Tiger Jam XI Benefit Concert in Las Vegas

    Chris Farina

    P.S. Kudos to Dave for wearing a golf glove during his Tiger Jam set.

    11th Annual Tiger Jam to Benefit the Tiger Woods Foundation - Show and Backstage

    Lester Cohen

    P. Diddy - 2009

    Tiger Jam 2009 With No Doubt

    Lester Cohen

    No Doubt - 2009

    Tiger Jam 2009 With No Doubt

    Lester Cohen

    Ben Roethlisberger - 2009

    Tiger Jam 2009 With No Doubt

    Lester Cohen

    Tony Romo - 2012

    AT&T Pebble Beach National Pro-Am - Final Round

    Jeff Gross

    AT&T Pebble Beach National Pro-Am - Round Two

    Ezra Shaw

    AT&T Pebble Beach National Pro-Am - Round One

    Jeff Gross

    Twinning.

    Jon Bon and some guy from American Idol

    2012 Tiger Jam

    Ethan Miller

    Jimmy Fallon - 2014

    The Tonight Show Starring Jimmy Fallon - Season 1

    NBC

    "You know who hasn't won 14 majors, Jim?"

    Airpods Wahlberg - 2019

    Genesis Open - Preview Day 3

    Stan Badz