Haal Too Well
Jake Gyllenhaal has appeared on a variety of talk shows, which fans are revisiting after Taylor Swif...
Hi, Just Some Jake Gyllenhaal Late-Night Show Clips For No Reason At All

Definitely not because I'm feeling emotionally crushed by the new "All Too Well" lyrics.

Jason Kempin/Getty Images Entertainment/Getty Images

*Removes AirPods* Sorry, what did you say? I couldn’t hear you, I was listening to Red (Taylor’s Version). Oh, you said you recently developed a curiosity about Jake Gyllenhaal’s oeuvre of late-night appearances? Hmm! That’s so funny — I was actually just thinking the same thing.

You know, now that you mention it, Gyllenhaal is widely rumored to be the source of inspiration behind Taylor Swift’s iconic 2012 ballad “All Too Well.” They reportedly dated from October to December 2010. Gyllenhaal never publicly addressed the song, and although Swift never confirmed who she was writing about, she did serve up plenty more heartbreaking details in her new 10-minute recording that dropped on Nov. 12.

For example, one lyric calls out her unnamed ex for putting on an act around her family: “You who charmed my dad with self-effacing jokes/Sipping coffee like you’re on a late-night show.” (Great song, 10/10, I can’t wait to scream-sing this at karaoke after my next breakup.)

Anyway, I rounded up a few clips of Gyllenhaal on a variety of late-night shows. Since we happen to share the same weirdly specific interest, I did us both a favor and took notes based on some totally random criteria. Are you ready for it?

The Tonight Show Starring Jimmy Fallon: Sept. 28, 2021

Sadly, Gyllenhaal’s dog Atticus wasn’t feeling all too well recently. As the actor told Fallon, the German Shepherd’s prostate issues led him to be neutered this year at the age of 7. Following the suggestion of a veterinarian, Gyllenhaal bought the pup “neuticles” — prosthetic testicles that let a dog "retain its natural look and self-esteem,” per the company’s website.

The procedure was apparently a success. "He's great. He's fine. He's healthy. He's happy. He has no recollection whatsoever," Gyllenhaal told Fallon.

Coffee? Yes.

Self-effacing jokes? Yes. He starred in the 2017 Broadway musical Sunday in the Park with George, and geeked out about how cool it was to be on Spotify. But his lengthy last name doesn’t fit neatly on the app’s display, so he suggested he should simply be cut from the credits.

My emotional state after watching this? Reminiscing about that one time in college when I saw Gyllenhaal walking Atticus outside NYU’s journalism building. Now, years later, upon learning he opted to give the dog “gorilla-sized” neuticles, my cheeks are turning red, kind of like a little kid with glasses in a twin-sized bed.

Conan: Sept. 21, 2017

This memorable entry into the canon of Jake Gyllenhaal Late-Night Show Appearances showcases the actor poking fun at himself for everything from his emo phase to his lack of computer skills (he claimed he doesn’t know how to copy and paste, though that feature became popular in 1983, when he was just 2 years old).

Coffee? No.

Self-effacing jokes? When Conan O’Brien asked Gyllenhaal if Holeshot, his high school boy band (yes, really), was any good, he simply cleared his throat and looked away with flawless comedic timing.

My emotional state after watching this? I might be OK, but I’m not fine at all. This led me down a research rabbit hole, googling Holeshot and wondering if it ever produced any cool indie records.

The Late Show with Stephen Colbert: Sept. 15, 2015

Amy Schumer and her sister Kim Caramele once rented out Gyllenhaal’s apartment. After a few drinks, she discovered a birthday cake in the actor’s freezer and filmed herself eating it. She showed off the video on Colbert, and days later, Gyllenhaal addressed the incident on the same show.

The late-night host gave the actor the opportunity to make a sassy comeback: dramatically biting into a cake of his own. Like revenge, birthday cake is a dish best served cold.

Coffee? Yep.

Self-effacing jokes? He could barely keep a straight face while saying, “People don’t know this — everyone in Hollywood just lives in the same house. That’s why we’re all so nice to each other. That’s why we love each other so much.” Sure!

My emotional state after watching this? Hungry. I want a big slice of birthday cake, and when I’m done eating, I’d wash it down with a nice maple latte.

Late Night with Seth Meyers: July 23, 2015

After chatting with Meyers in front of the studio audience, Gyllenhaal “forgot his phone” on set. Meyers walked into Gyllenhaal’s dressing room to return it, only to discover the actor is totally bald under a luscious toupée.

Coffee? No.

Self-effacing jokes? He barely utters a peep in this clip, but donning a bald cap for the sake of laughs definitely counts.

My emotional state after watching this? I hope he can find peace with himself, no matter what state his follicles are in, but I worry he might miss the feeling of wind in his hair.

The Tonight Show with Jimmy Fallon: Oct. 30, 2014

Gyllenhaal stopped by The Tonight Show to talk about his sister Maggie Gyllenhaal’s incredible Broadway debut, The Real Thing. Supportive!

Coffee? Yep.

Self-effacing jokes? He claimed his sister can smell him from all the way across a theater.

My emotional state after watching this? Concerned about Jake’s possible lack of deodorant, thrilled for Maggie’s success, but mostly deeply interested in her collection of winter accessories.

Anyway! It’s been so lovely to bond with you over our mutual interests and hobbies. I apologize if any of my comments came across as casually cruel — I was just being honest. I’m gonna run, I need to finish listening to this album. Bye!