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Perry — who tragically passed away on Saturday at the age of 54 — was a virtual unknown when Friends debuted on NBC in 1994, but he quickly rocketed to stardom by crafting one of the most iconic comedy performances in TV history. Chandler was as unique as his name: He was never the most macho guy in the room, or the smoothest, either, but he was smart and funny, rattling off endlessly clever one-liners we’re still quoting to this day. Plus, he proudly wore his insecurities on his sleeve, which made him immensely relatable despite all of his glaring inadequacies. There had never been anyone on TV quite like him, and there hasn’t been since.
In honor of Perry’s life and career, we’re looking back at the 10 Friends episodes that best represent the sheer excellence of his performance as Chandler Bing. (Can you believe he never won an Emmy? Could that be any more wrong?) From his early days stumbling through romantic mishaps to him finally finding love with his pal Monica, we’ve picked out Chandler’s greatest highlights and lowlights — and if you want to check any of these out, all 10 seasons of Friends are now streaming on Max. (TBS will also be running a Friends marathon of Chandler episodes from Nov. 1 to Nov. 5.)
Read on to see which episodes made our list of The Best of Bing — and hit the comments to share your own personal favorites.
“The One With the Blackout” (Season 1, Episode 7)
We were still just getting to know Chandler Bing when a blackout hit the city and, in his words, he got “trapped in an ATM vestibule with Jill Goodacre!” His ill-fated attempts to look cool in front of the Victoria’s Secret model were Chandler at his most awkward (“Gum would be perfection”), but he eventually won her over, with Perry flashing a casual charm worthy of a rom-com leading man. Chandler got a kiss on the cheek… which may have been his top romantic highlight in the first four seasons.
“The One After the Super Bowl, Part 2” (Season 2, Episode 13)
Friends was such a huge phenomenon at this point that they got a special post-Super Bowl episode with oodles of A-list guest stars, including Julia Roberts as Chandler’s old classmate Susie Moss. Roberts was the biggest movie star on the planet at the time, but Perry nimbly held his own in their scenes together, sporting a sparkling chemistry that we wish lasted longer than just one episode. Sadly, Susie only wanted revenge on Chandler for teasing her in school, and Chandler ended up stranded in a restaurant’s bathroom stall wearing nothing but her underwear.
“The One Where Chandler Can’t Remember Which Sister” (Season 3, Episode 11)
After Chandler got sloshed on Jell-O shots — with some truly inspired drunk acting from Perry — he ended up hooking up with one of Joey’s sisters. But as the episode title tells us, he was too blitzed to remember which one. His secret mission to ID the sister in question was a fantastic showcase for Perry’s frantic brand of physical comedy, trying to sleuth out the answer during a Tribbiani family dinner. It didn’t help, of course, that all of Joey’s sisters looked vaguely like Fran Drescher from The Nanny.
“The One Where Chandler Crosses the Line” (Season 4, Episode 7)
One of Chandler’s best pre-Monica romantic sparks was with Kathy, Joey’s actress girlfriend played by Paget Brewster. Chandler’s secret yearning for his best friend’s girl was totally wrong, of course, but also totally understandable, and the scenes where Chandler wrestled with his true feelings proved that Perry could be a more than capable romantic lead. (The next episode, with Chandler spending Thanksgiving in a box as penance, also showed that we didn’t even need to see Perry’s face or body for him to make us laugh.)
“The One With All the Rugby” (Season 4, Episode 15)
Or, as we refer to it, the Yemen episode. Chandler’s on-and-off romance with nasal Noo Yawker Janice brought out the best in Perry, and he hit new heights as Chandler was so desperate to break things off with her, he made up an elaborate lie about being transferred to Yemen for work. Perry made Chandler’s dilemma hilariously agonizing as he went to ridiculous lengths to keep the lie alive, even buying a ticket to Yemen and boarding the plane so Janice wouldn’t catch on. Probably still worth it, though.
“The One Where Everyone Finds Out” (Season 5, Episode 14)
One of the best Friends episodes ever featured an all-time great performance from Perry, as Chandler and Monica were still keeping their romance secret, leading to a complicated double-bluff where he and Phoebe had to pretend to be hot for one another. The result was an exquisitely awkward farce where Chandler was forced to seduce his friend… and then finally gave up and admitted he’s in love with Monica, with Perry flashing a heartwarmingly genuine brand of affection. Just don’t let Ross find out, OK?
“The One With the Proposal, Part 2” (Season 6, Episode 25)
Chandler’s tender romance with Monica allowed Perry to reveal a newfound vulnerability in his jokey character, and that was on full display in the Season 6 finale, with Chandler panicking that he might lose Monica to her ex Richard. He didn’t, though, and their mutual proposal, with Monica getting too emotional and Chandler taking over, was Friends at its most earnestly heartfelt. Chandler usually can’t resist going for the punchline, but his slow dance with Monica to “Wonderful Tonight” was refreshingly sincere instead.
“The One With the Engagement Picture” (Season 7, Episode 5)
Chandler didn’t stop being a goofball just because he landed Monica, you know. Their efforts to take a half-decent photo for their engagement ended in disaster when they realized Chandler doesn’t know how to smile, with Perry twisting his face into a gruesome snarl. They eventually worked around it, though — by having Joey stand in for him.
“The One With Monica & Chandler’s Wedding, Part 2” (Season 7, Episode 24)
Monica and Chandler’s big day had its share of sitcom complications — the groom’s cold feet, Joey’s delays on a movie set — but those all melted away when they finally got to the altar and looked into each other’s eyes. The actors’ voices quaked with emotion as Chandler and Monica read their vows and pledged their love, making this one of our favorite TV weddings of all time.
“The One Where Chandler Takes a Bath” (Season 8, Episode 13)
He played Chandler Bing for a decade, but Perry proved he could still surprise us in this installment, with Chandler developing a taste for luxurious bubble baths. The sight of him unwinding to the gentle sounds of Enya was a delight, and it hilariously culminated in the rest of the gang invading the bathroom and interrupting his bliss. Even late in the series’ run, Perry still had his comedy fastball — and in our hearts, he always will.
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