Jimmy Fallon Shirtless Photos: Gay or Crossdressing Enthusiast?

Jimmy Fallon Young, Shirtless, and Underwear Photos. This post ain’t getting some love among you Famewatchers so we decided to update it to bring you some pics of our Jimmy as a youngin. He’s actually really, really cute back then which makes us understand why the gorgeous and fabulous Nicole Kidman wanted to hang with him at one time.

jimmy fallon young hunk

jimmy fallon young

jimmy fallon young and hot

A young Jimmy with his prom date back in high school:

jimmy fallon young high school stud

Now, since we are all about celebrities and their underoos, here’s Jimmy posing in his boxer briefs. First, here’s the late night host trying to “seduce” then San Francisco Giants pitcher Madison Bumgarner who is now with the Arizona Diamondbacks.

jimmy fallon underwear for madison baumgarner

And here’s Jimmy with Joe Jonas trying to recreate the latter’s modeling pose for Guess Underwear:

jimmy fallon underwear with joe jonas

jimmy fallon underwear model

Jimmy Fallon Shirtless Photos: Gay or Crossdressing Enthusiast (15 October 2013). If there is a contest on the Most Number of Times a Male Hollywood Celebrity Dressed Up as a Woman, we have no doubt that late night talk show host Jimmy Fallon will win it hands down. Doesn’t he look pretty in the black sleeveless gown he’s wearing above?

jimmy fallon wearing womans dress

Want more of Jimmy’s cross-dressing photos? Check him out as a teen girl.

jimmy fallon crossdressing

jimmy fallon as sara from nickelodeon

Jimmy as a mom dancer in The Evolution of Mom Dancing with First Lady Michelle Obama, then as crazy lady Michelle Bachman and, finally, as Hilary Swank.

jimmy fallon as a woman

jimmy fallon as michelle bachman

jimmy fallon as hilary swank

We’re pretty sure there are other photos out there of Jimmy wearing women’s clothes but we already have enough. We won’t be surprised if he actually wears these clothes in private because why not. Hehe. Want more men wearing women’s dresses?

Not unexpectedly, Jimmy’s enthusiasm for crossdressing prompted some of you to google whether the TV funny man is gay. Well, to paraphrase Sheldon Cooper, “He’s not gay. His mother had him tested.”

The website jimmyfallon.com (we’re assuming this is his very own official website) also asks the question and answers it too: “Even if he IS ‘married’, he could still be a closet g*y. Many, many g*y people ‘marry’ the opposite sex to hide their homos*xuality. You don’t really need to see his interests, just look at his face (soooooooo g*y), body, and body language. The word g.a.y. is written right across him.”

Now, some of you are not at all interested in Fallon’s gayness or his crossdressing shenanigans but are interested in his shirtless photos. Don’t fret coz we’ve got pics for you too. Check ’em out:

jimmy fallon shirtless with terry crews

jimmy fallon shirtless

jimmy fallon shirtless

Looking for a Jimmy Fallon underwear photo? We’re afraid this is the only one you will find in the history of ever.

jimmy fallon underwear.jpg

On the all-important boxers or briefs question asked of all male celebrities, he revealed in an interview with Bravo TV that “he switches it up between boxers, briefs and boxer-briefs but normally wears boxer-briefs”.

Jimmy Fallon Shirtless Photos and Crossdressing Enthusiast. Posted 15 October 2013. Last updated: September 24, 2021 at 5:00 am.