King of Swing: Derek Jeter's Best Pop Culture Moments

As the Yankees shortstop closes in on his 3,000th hit, check out his top highlights away from the diamond.

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Overrated? Fuhgeddaboutit. Derek Jeter has five rings, a track record of hitting the baddest chicks (no C-Breezy), a huge castle on the beach, and a crazy amount of endorsement cake, so hate if you want—the Captain doesn't care. He's accomplished all this while under the New York media microscope, and has managed to elude major controversy the whole time; Jeter is all class. Unlike some MLB superstars (ahem, A-Rod), the Yankee captain isn't some cornball, either. The sports icon has made a cameo on Seinfeld, appeared in skits and commercials with award-winning actors, and even received a lyrical shout-out from Foxy Brown. So, as he approaches the exclusive 3,000 hit club (only 14 12 11 10 9 7 6 4 3 2 to go CONGRATS TO THE CAPTAIN!), we take a look at Derek Jeter's Best Pop Culture Moments.

Seinfeld

DATE: 11/21/1996
COMPLEX SAYS: Fresh off his first championship, reigning American Leage Rookie of the Year Derek Jeter and teammate Bernie Williams take hitting lessons from George Costanza. At first, it seems like ol' Georgie boy is full of shit, but then he proceeds to put on a show and takes a shot at Jeter and Williams for letting the Series go six games. The Yankees won three of the next four World Series, none of them went six. Go figure.

The Ladies' Man

DATE: 1997-present
COMPLEX SAYS: Girls, girls, girls. Forget Jigga or Mötley Crüe, neither of them have anything on Derek Jeter's bevy of beauties. And those are just the girls we know about. Jeter's a throwback to the days when a star athlete can bag a hottie and not ruin his rep in the process. No pics of his junk are floating around and he hardly ever gets caught on scene with one of his broads. Now he's engaged to Minka Kelly. Straight class. #swagonatrillion


It's Gotta Be the Shoes

DATE: 1999
COMPLEX SAYS: Derek Jeter was the first baseball player to be under Jordan Brand. He was rocking PE Jordan spikes before we knew what the hell was going on; "Are those the 14s he's rocking?" It's only right that the two legends would link up—takes a winner to know one.

ESPY Skit with Samuel L. Jackson

DATE: 2/12/2001
COMPLEX SAYS: It's all starting to make sense. No. 2 was just a young padawan trying to learn the ways of the Jedi until he crossed over to the dark side of the force. Not to mention, his new pad is as big as the Death Star. The Empire strikes back!

Hosts Saturday Night Live

DATE: 12/1/2001
COMPLEX SAYS: Remember when SNL was consistently funny and the Tri-State area had delicious Mexican food? OK, so maybe that last part isn't true. But, in this was a classic SNL episode, Jeter appears alongside Will Ferrell and Jimmy Fallon and later dresses in drag. Yeah, the cross-dressing was kind of suspect, but have you hooked up with Miss Universe? *Sigh* Us neither.

Visa Ad with The Boss

DATE: May 2003
COMPLEX SAYS: George Steinbrenner's public criticism about the Yankee captain partying too much served as the basis for this Visa commercial. The only thing we can't co-sign in this ad is believing you can find Jeter in a conga line at the club. Now, grinding up on Gabrielle Union while on vacation in the Bahamas? Yeah, that sounds more like it.

Gatorade Ad with Harvey Keitel

DATE: 2007
COMPLEX SAYS: Harvey Keitel channels Pulp Fiction and Reservoir Dogs, which makes this ad totally badass. He plays the devil on Jeter's shoulder and talks him into stealing. All of this just for a Gatorade commercial? Thank you Based God!

This Is SportsCenter

DATE: May 2010
COMPLEX SAYS: In this clip, ESPN hits us with another classic promo. Fresh off beating the Phillies to earn his fifth ring, Derek Jeter shows off his comedic timing and totally disregards the hairy ass green dude in the room Phillie Phanatic. Payback's a bitch, we guess?

Cameo in The Other Guys

DATE: 8/6/2010
COMPLEX SAYS: After all the actresses he's smashed, film seems like a natural transition for Mr. November. In this cameo, Marky Mark plays out every Red Sox fan's wet dream as he shoots Derek Jeter during the World Series. Quote to remember: "He's a bi-racial angel! You should've shot A-Rod!" *DEAD*

GQ Covers

DATE: September 1998, April 2000, April 2011
COMPLEX SAYS: Every dude wants to be him and every chick wants to be with him. You know you're that dude when you get a GQ cover. You know you're Derek Jeter when you get three. You also know you're not bitchmade when you avoid trashing fellow MLB stars in a cover story interview. We see you, A-Rod.

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