News
A visual history of Tiger Woods' best (and most painfully awkward) celebrity encounters
![Tiger Jam 2011](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c65a25905c72e2cbf557723_KeithUrbanMayer.jpg.rend.hgtvcom.966.544.suffix/1573167747568.jpeg)
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](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c6588a828e3d46a86afece5_Leno2.jpg.rend.hgtvcom.966.644.suffix/1573167705717.jpeg)
NBC
Say yes to the vest.
Twister-era Bill Paxton - 1997
![The Tonight Show with Jay Leno - Season 6](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c65854c05c72e2cbf557716_Paxton.jpg.rend.hgtvcom.966.644.suffix/1573167718852.jpeg)
NBC
Kevin Costner -1997
![AT&T National Pro-Am](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c6585f828e3d46a86afece3_KCos2.jpg.rend.hgtvcom.966.644.suffix/1573167724211.jpeg)
Andy Lyons
"So what did you think of Tin Cup?"
The Dream Team -1998
![The Tonight Show with Jay Leno](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c6585b76b8e772d393cbab0_Leno.jpg.rend.hgtvcom.966.644.suffix/1573167731204.jpeg)
NBC
Kid Rock and Pamela Anderson - 2001
![Tiger Jam IV](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c658ea705c72e2cbf55771d_GettyImages-94676398.jpg.rend.hgtvcom.966.773.suffix/1573167742518.jpeg)
L. Cohen
Samuel L. Jackson - 2001
![The Ninth Annual ESPY Awards](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c6588256b8e772d393cbab6_GettyImages-2248324.jpg.rend.hgtvcom.966.690.suffix/1573167732066.jpeg)
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](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c6586426b8e772d393cbab2_CarsonDaly.jpg.rend.hgtvcom.966.644.suffix/1573167725829.jpeg)
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](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c658c1f05c72e2cbf557718_Train.jpg.rend.hgtvcom.966.544.suffix/1573167737358.jpeg)
Ethan Miller
Stevie Wonder - 2005
![Tiger Jam VIII - Show](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c65895c6b8e772d393cbaba_StevieWonder.jpg.rend.hgtvcom.966.690.suffix/1573167739140.jpeg)
L. Cohen
Terri Hatcher and Sam Jackson - 2006
![Tiger Jam IX Benefit Concert - Backstage and Show](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c6586fe3db98a219c79866e_TerriHatcher.jpg.rend.hgtvcom.966.644.suffix/1573167730246.jpeg)
L. Cohen
Sting - 2006
![Tiger Jam IX Benefit Concert - Arrivals](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c6589036b8e772d393cbab8_Sting.jpg.rend.hgtvcom.966.773.suffix/1573167738295.jpeg)
L. Cohen
Terri Hatcher and John Mayer -2007
![Tiger Woods Learning Center Block Party](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c6587b96b8e772d393cbab4_MayerHatcher.jpg.rend.hgtvcom.966.725.suffix/1573167728551.jpeg)
Lester Cohen
Your vertical stripes are a wonderland.
Mike - 2007
![PGA TOUR - 2007 Wachovia Championship - Pro-Am](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c659177d49c9c16357c2d07_GettyImages-76348881.jpg.rend.hgtvcom.966.690.suffix/1573167702994.jpeg)
Sam Greenwood
Will Ferrell - 2007
![Tiger Wood's 10th Annual "Tiger Jam"](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c658f8a3db98a219c798676_WillFerrell.jpg.rend.hgtvcom.966.966.suffix/1573167741710.jpeg)
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"](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c65906e6b8e772d393cbabf_Daughtry.jpg.rend.hgtvcom.966.644.suffix/1573167714976.jpeg)
Lester Cohen
Justin Timberlake - 2008
![2008 ESPY Awards - Show](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c65a36728e3d46a86afecef_GettyImages-81958548.jpg.rend.hgtvcom.966.773.suffix/1573167707415.jpeg)
Kevin Winter
Never. Sleeping. Again. #Unchained
Eddie Van Halen - 2008
![11th Annual Tiger Jam to Benefit the Tiger Woods Foundation - Arrivals](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c6589c63db98a219c798670_EVH.jpg.rend.hgtvcom.966.644.suffix/1573167734583.jpeg)
Lester Cohen
David Lee Roth- 2008
![USA - Tiger Jam XI Benefit Concert in Las Vegas](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c6589dd3db98a219c798672_DavidLeeRoth.jpg.rend.hgtvcom.966.690.suffix/1573167735418.jpeg)
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](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c658a183db98a219c798674_DavidLeeRoth2.jpg.rend.hgtvcom.966.966.suffix/1573167744209.jpeg)
Lester Cohen
P. Diddy - 2009
![Tiger Jam 2009 With No Doubt](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c658b42d49c9c16357c2d03_Diddy.jpg.rend.hgtvcom.966.690.suffix/1573167739982.jpeg)
Lester Cohen
No Doubt - 2009
![Tiger Jam 2009 With No Doubt](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c658ba328e3d46a86afece7_NoDoubt.jpg.rend.hgtvcom.966.644.suffix/1573167706580.jpeg)
Lester Cohen
Ben Roethlisberger - 2009
![Tiger Jam 2009 With No Doubt](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c658f0205c72e2cbf55771f_BigBen.jpg.rend.hgtvcom.966.690.suffix/1573167746737.jpeg)
Lester Cohen
Tony Romo - 2012
![AT&T Pebble Beach National Pro-Am - Final Round](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c658daf6b8e772d393cbabc_Romo2.jpg.rend.hgtvcom.966.644.suffix/1573167745927.jpeg)
Jeff Gross
![AT&T Pebble Beach National Pro-Am - Round Two](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c658dbd28e3d46a86afece9_Romo3.jpg.rend.hgtvcom.966.644.suffix/1573167745076.jpeg)
Ezra Shaw
![AT&T Pebble Beach National Pro-Am - Round One](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c658dccd49c9c16357c2d05_GettyImages-138596169.jpg.rend.hgtvcom.966.644.suffix/1573167740863.jpeg)
Jeff Gross
Twinning.
Jon Bon and some guy from American Idol
![2012 Tiger Jam](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c6590313db98a219c798678_JonBonDavidCook.jpg.rend.hgtvcom.966.725.suffix/1573167709024.jpeg)
Ethan Miller
Jimmy Fallon - 2014
![The Tonight Show Starring Jimmy Fallon - Season 1](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c6590af6b8e772d393cbac1_Fallon.jpg.rend.hgtvcom.966.644.suffix/1573167709864.jpeg)
NBC
"You know who hasn't won 14 majors, Jim?"
Airpods Wahlberg - 2019
![Genesis Open - Preview Day 3](http://golfdigest.sports.sndimg.com/content/dam/images/golfdigest/fullset/2019/02/14/5c65940628e3d46a86afeced_GettyImages-918242998.jpg.rend.hgtvcom.966.690.suffix/1573167733737.jpeg)
Stan Badz