Looking back at the Yankees’ appearances on Saturday Night Live

Just a few days after celebrating the Cubs’ first World Series victory in 108 years, Anthony Rizzo, Dexter Fowler, and David Ross traveled to New York to make a couple appearances on the most recent episode of Saturday Night Live. They twerked, sang with Bill Murray, and honestly were the only highlights of a lackluster episode (#TVHotTakes). If Fowler does not return to the Cubs after free agency, then those will be the last images of him with them, so that’s mildly amusing on its own.

Baseball players and humor don’t typically mix (save for “Foul Territory” and Brandon McCarthy’s Twitter), but the Yankees have made their share of SNL appearances in the show’s long history. Although Derek Jeter’s hosting gig is relatively well known, he’s far from alone.

1998 Yankees

After sweeping the Padres to wrap up the most dominant season in MLB history with a combined 125 wins, a few Yankees stopped by SNL to crash Ben Stiller’s monologue. Tino Martinez, Chili Davis, Graeme Lloyd, David Cone, and David Wells gradually show up on-screen as Stiller “confuses” the applause for himself. Simple concept, but it works, and Wells making faces behind Stiller is exactly something he would do. He’d be back.

Billy Martin

On May 24, 1986, during one of the several times he was between Yankees managerial gigs, the fiery skipper actually hosted SNL (to be fair, he co-hosted with actress Anjelica Huston). A running gag of the night was Martin gradually losing his cool, from dismissing an insult by Anthony Michael Hall in the monologue (“The old self-destructive Billy Martin would have punched a guy out for saying something like that.”) to setting the cast’s dressing room ablaze in retaliation for Lorne Michaels firing him as co-host during the last sketch.

In a somewhat amusing twist, Martin’s final act was prophetic. The credits at the end of the show teased “Who will survive?” and put question marks after the names of everyone involved, and as it turned out, summer 1986 brought a huge turnover to the show. Michaels saved Jon Lovitz in the sketch, leaving everyone to “burn,” and only Nora Dunn and Weekend Update anchor Dennis Miller returned from the main cast, a group that included future star Robert Downey. That led to the hiring of Phil Hartman, Dana Carvey, and Jan Hooks, ushering in a brilliant new era for the show.

Derek Jeter

Derek Jeter’s Taco Hole, in all its glory. Jeter hosted SNL at age 27 shortly after the 2001 World Series (with topical musical guest BUBBA SPARXXX), and... to be frank was pretty much just his classic vanilla self. In the monologue, he injured the audience with baseballs meant to be souvenirs off the bat. There was also the glorious taco hole sketch, a weird commercial where he was supposed to be the third Iglesias brother who only did spoken word, and a “Derek Jeter sucks”/”No I don’t” point/counterpoint on Weekend Update with Red Sox fan and future late night host Seth Meyers.

Jeter later appeared on SNL’s 40th anniversary special in February 2015 introducing the sports segment with Peyton Manning. The most memorable Jeter sketch was truly stolen by two dynasty teammates.

David Wells and David Cone

Neither Boomer or Coney officially hosted SNL, but they’ve appeared more than anyone else, which is fitting given how ridiculous they are. As previously mentioned, they crashed Ben Stiller’s monologue in 1998, made a brief appearance with Billy Crystal’s Fernando character during the 25th anniversary special in ‘99, and then cameoed in Jeter’s hosting gig, though neither were with the Yankees at the time. Still, seeing them all in drag sure is... a thing. (Aside: As good as Amy Poehler is, woof, those Chuck Knoblauch jokes did not age well.)

On a lighter note, the duo returned to SNL once more in 2015 for the 40th anniversary after party. Jay-Z confused Wells for Curt Schilling. Outstanding.

George Steinbrenner

Yes, this really happened. George Steinbrenner hosted SNL on October 20, 1990. He did it while he was suspended from baseball for hiring a gambler to dig up dirt on his own star, Dave Winfield. He did it on the very same night that the Cincinnati Reds won the World Series on an opposing network. Sounds about right.

In his 2010 biography of Steinbrenner, Bill Madden recounted a report by Bob Raissman of the Daily News of Steinbrenner behind the scenes. It was odd:

“He was all by himself, in the semi-darkness at the back of the set, playing a piano and softly singing ‘The Shadow of Your Smile.’ It was eerie. He just seemed to be in total peace with himself.”

Alrighty then.

(Steinbrenner also appeared with Crystal’s Fernando character, though that was outside SNL.)

Yankee Superheroes

Technically there are no Yankees in this since this animated short from October 2003 was voiced by Robert Smigel, but there are so many terrific Yankee references here, it belongs. My favorite parts are probably when Wells is punched at the bar and loses a tooth, referencing a real life incident from the year before, and when Steinbrenner haggles woebegone Devil Rays manager Lou Piniella for up-and-comer Rocco Baldelli. (Also “feed ‘em Zimmer.”)

I would question how the cardboard cut-out Yankees scored five runs off the Devil Rays in the first place, but then again, the 2003 Devil Rays were really bad. So...

Yogi Berra and Dave Winfield

This is a shorter appearance, but in an October 1984 episode hosted by “Mr. Baseball,” Bob Uecker, these two Hall of Famers made filmed appearances. It was a short about two fictional Negro League players named Leonard "The Rooster" Willoughby and "King Carl" Johnson (you can watch it here; I didn’t embed it because it automatically plays otherwise). The funny thing is that they could have gone much crazier with the nicknames given the era.

It was made by Crystal and Christopher Guest in the mockumentary style of This is Spinal Tap, and yeah, it hasn’t aged well. It’s also not very funny, save for Yogi Berra talking about “Smelt Night.” This later appeared as part of an oddball episode in March 1985 where Roger Ebert and Gene Siskel critiqued each sketch. The ‘80s sure were a time.

Roger Clemens/1994 Yankees

Jason mentioned this sketch in a post he did in February on the many strange film and TV roles of Roger Clemens. Since Clemens was on the Red Sox at the time, I wouldn’t normally include it (hence the omission of Johnny Damon and a delightfully random handful of other past/future Yankees in ‘97).

However, it does name drop a ton of ‘94 Yankees, so good enough. Although maybe it’s a little depressing that this exists since part of the joke was that all these baseball players were free that fall due to the strike that cancelled a possible World Series trip for the Yankees. Oh well.

Special thanks to SNL Archives and SNL Transcripts.