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Derek Jeter Dressed in Drag for a Classic SNL Skit

Ask anyone in the world who the most famous baseball player was during the 1990s and 2000s and they’ll tell you one name: Derek Jeter. Mr. November won five World Series in the pinstripes and became renown for his clutch hitting and signature plays.

The former New York Yankees shortstop was bigger than baseball, however. He was a celebrity that everyone adored. The Captain’s face has been all over TV, from appearing in Seinfeld and starring in movies such as The Other Guys (2010) and Anger Management (2003).

Before retiring in 2014 with more than 3,000 hits under his belt, the nearly unanimous Baseball Hall of Fame inductee proved in 2001 he was just as good at cracking jokes as he was cracking line drives.

In fact, Derek Jeter’s time hosting Saturday Night Live in 2001 ranks right up there with Peyton Manning’s hilarious stint as far as athletes go.

Derek Jeter Hosts SNL in 2001

Derek Jeter’s Taco Hole pic.twitter.com/nE2hi2mqN4

— Jimmy Traina (@JimmyTraina) April 9, 2017

After the Yankees won the World Series in 2001, Jeter headed to NBC studios to host the famous comedy sketch show in December in an appearance shared by musical guests Shakira and Bubba Sparxxx.

To be honest, Jeets was genuine and funny as hell.

In Jeter’s opening monologue, he scorched line drives at audience members and took out a camera. He starred as the third Iglesias brother in a commercial and argued with Red Sox fan and future late night host Seth Meyers in a “Derek Jeter sucks” point/counterpoint as part of Weekend Update.

Jeter also dusted off his pipes. He sang alongside Will Ferrell and Jimmy Fallon as the owner of a Mexican restaurant called “Derek Jeter’s Taco Hole.”

“I was scared to death … I really was,” he said after hosting SNL.

But the best skit from this episode, and one of the best any athlete has taken part in, was the “Yankee Wives” skit.

Derek Jeter Dresses in Drag on SNL

Derek Jeter hosted SNL on this day in 2001. pic.twitter.com/w5wwQsYAyq

— Kevin Sullivan (@SullivanYES) December 1, 2019

That’s right. Derek Jeter donned a wig, applied his make-up and slipped into a sexy dress in SNL’s “Yankee Wives” sketch.

Jeter is introduced as Candy Soriano, Yankees outfielder Alfonso Soriano’s wife. He then joins a group of player wives — Amy Poehler as Chuck Knoblauch’s wife, Rachel Dratch as Roger Clemens’ wife, Maya Rudolph as Mariano Rivera’s wife and Ana Gasteyer as Bernie Williams’ wife — to enjoy the game.

Poehler cracks a joke about Knoblauch’s marriage, which isn’t so funny now considering what happened between he and his wife in real life. The skit also takes a shot at baseball wives by suggesting all they do is watch baseball and make cookbooks.

At one point, Jeter hilariously roasts himself by saying he “looks like the Rock had sex with a muppet.”

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The absolute best part of the entire skit is when the two “skanks” walk up to the group. David Wells, who looks awfully bad in a dress but is hilariously awesome, and David Cone, who actually kind of pulls off that mini skirt and leopard print, join their teammate in the sketch as groupies after the Yankee wives’ husbands.

Cone asks Jeter if he’s Alfonso Soriano’s wife and then asks why he left his “tighty wighties” with her the previous night.

Cone told YES Network Jeter had no clue he and Wells were going to be in the skit.

“Once in a lifetime, it really was, to actually be a part of an actual skit and have lines,” Cone said. “Jeter didn’t know we were coming out. You can tell by the look on his face.”

Jeter had so much fun on the TV show, he reappeared on SNL for its 40th anniversary special with Manning.

Plenty of athletes and sports figures have had cameos on SNL, including Tom Brady, Michael Jordan, LeBron James, Hulk Hogan and George Steinbrenner. But let’s always appreciate the time Derek Jeter dressed as a girl and looked pretty good doing so.

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