While the other friends are home during a city blackout — singing the Carpenters’ “Top of the World” and meeting hot Italian neighbors — Chandler is stuck in an ATM vestibule with model Jill Goodacre. He does his best to convey his situation to Joey over the phone (a teeth-clenched “I’m stuck in an ATM vestibule with Jill Goodacre!”) and has zero chill, telling her that “Gum would be perfection” before nearly choking to death. The Season One scene remains beloved, and it speaks volumes to Perry’s performance that Gen Z fans quote it — even if they are unfamiliar with the concept of blackouts and probably have to google Jill Goodacre.

No one loves to smoke cigarettes more than Chandler (except maybe Gunther). While his love for nicotine resurfaces several times in the series, the first mention in the show’s third episode proves that Perry had the acting chops right from the show’s beginning (honorable mention goes to the Hypnosis Tape, which hasn’t aged too well). Chandler helps Joey rehearse for an audition by properly teaching him how to smoke, but his first drag — where he releases an “Ohhh my godddd” — brings back his addiction.

Unable to properly break up with Rachel’s boss Joanna (“I’ll give you a call, we should do it again some time!”) Chandler gets stuck at the Bloomingdale’s office — literally. Joanna (played by Alison La Placa) kinkily handcuffs Chandler to her desk while she’s out in a meeting, and Rachel contemplates whether to let him free or not. The peak is three minutes in, when the file cabinet she relocated him to slams in his head. RIP to Joanna, who gets hit by a cab and dies a few episodes later (at least it was a good day for Sophie).

“Sir, a ticket to Yemen is $2,100 and we don’t take library cards.” Maggie Wheeler appeared in 19 episodes of Friends, but it never got old seeing Janice reemerge into Chandler’s life — whether it was through one of the earliest examples of online dating or a run-in at the fertility clinic. But his fake move to Yemen in an effort to get rid of her is the most hilarious, and it’s not even the main plot of the episode (“The One With All the Rugby,” Season Four). We only wish that the following episode included a scene of him trying to get back home to New York.

Every season of Friends has a Thanksgiving episode, which is Chandler’s least favorite holiday thanks to some good old family trauma. In Season Four, after falling in love and making a move on Joey’s girlfriend Kathy, he pleads his friend’s forgiveness by trapping himself in a box. The B-plot of the episode, in which an eye-patched Monica hooks up with Richard’s son, is not nearly as funny as Chandler’s index finger poking out of the box, waving Kathy goodbye.

Heartbroken over Janice, Chandler gets wasted on vodka jello shots at Joey’s birthday party. In walks the seven Tribbiani sisters, who all look so much alike with their bushy brunette hair and red lips that Chandler asks Monica, “How many of that girl are you seeing?” (The best line in this episode comes from a leather-clad Cookie Tribbiani after Phoebe offers her a vodka cran: “That’s the same drink I made myself right after I shot my husband!”) Chandler winds up fooling around with Joey’s sister that night, only he can’t remember which one — and his quest to identify Mary-Angela the next day, over tiramisu at the Tribbiani dinner table, goes horribly wrong. The lesson: Do not hook up with your Italian friend’s sister, or you will face the wrath of Cookie. All six friends were incredible at acting drunk (especially Courteney Cox in Season Seven) but with his green tongue and slurring delivery, Perry knocks it out of the park.

Chandler at work is an overall bit in the series, going well beyond the famous joke that none of the friends know what he does for a living. He can’t be mature in interviews. He falls asleep in a meeting and gets relocated to the Tulsa office. He has a horrible work laugh. His boss regularly sexually harasses him by smacking his ass. But nothing is better than when he reveals that his coworker Bob once called him Toby, and he didn’t correct him because he wanted a donut. Now five years have passed, and it’s too late to correct him, so when Bob asks Toby to get revenge on some guy named Chandler for preventing his promotion, he destroys his own office.

It’s nearly impossible to choose a single hilarious moment from Monica and Chandler’s affair (“The One Where Everybody Finds Out” is out of the running, since it’s a group effort). Joey, the only one (for a while) who knows about their new relationship, is usually to blame for any traces Monica and Chandler leave behind — underwear on the couch, a sex tape, naked photos. But it’s Chandler who royally screws up in the beginning of Season Five, when he kisses Monica goodbye in front of Phoebe and Rachel and decides to kiss all of them to make it less weird: “I was just trying to bring a little culture to the group!”

Throughout each of the ten seasons, Chandler struggled with his masculinity. The constant joke that he gives a gay “quality” has not aged well, but this Season Eight moment has — especially in the era of wellness and self-care. Monica introduces him to the concept of baths, and he relaxes to Enya’s “Who Can Say” while clutching his manly toy boat. He soon becomes addicted and steals Monica’s bath, only to have the friends huddle in the bathroom as Rachel and Ross reveal they’re having a girl. For a later season, during the awkward arc of Joey’s crush on Rachel, it remains a highlight. 

There’s a lot to unpack with Chandler’s childhood trauma. From his fear of commitment to his hatred of Thanksgiving to his bizarre anti-dog stance, it could be an entirely separate list. But we’ll narrow it down to the fact that he’s unable to cry, even during sad movies like Bambi (“It was very sad when the guy stopped drawing the deer”) or at the thought of disabled animals (“Cry? I just found a talking puppy, I’m rich!”). Hardcore fans have noticed a plot hole, though, as he cries several times throughout the series.