The Five Worst ‘Friends’ Episodes That Aren’t ‘The One With Chandler’s Dad’

Judging from its widespread popularity and surprising longevity, Friends is no doubt one of the greatest TV comedies of all time — and perhaps the greatest to feature a random monkey character for no good reason.

But as beloved as the series remains to this day, the Friends canon isn’t without its clunkers. But in the spirit of positivity, we’d like to attempt to see if we can find some good in some of the less-esteemed Friends episodes. To help us with this endeavor, we spoke with two legit Friends experts: Kelsey Miller, author of I'll Be There For You: The One About Friends, and Jennifer Dunn, author of Friends: A Cultural History.

Most people agree that the very worst episode of Friends is “The One With Chandler's Dad,” in which Chandler’s estranged parent is revealed to be a trans Vegas performer, played by cisgender actress Kathleen Turner (who later stated that she wouldn't take the role today).

We’re going to put aside this particular narrative dumpster fire that even the show’s creators reportedly regret — although there are some positives to be found even in this episode. As Miller revealed, acknowledging that she herself is “a straight, white, cisgendered lady,” in researching the book, she discovered that this storyline was important to some people at the time, like writer Mey Rude, who told her, “Trans women were so starving to see themselves on screen. So, when we saw ourselves in a way that wasn’t absolutely terrible, it seemed like a great thing.”

And Dunn notes that “one redeeming moment that could be recognized” is the brief cameo by “Alexis Arquette, David Arquette’s sister, and a trans woman.” Her character also got to take Chandler down a peg.

As for the rest of the more dubious entries in the Friends-verse (not including clip shows, which are a whole other level of suckage), let’s talk about…

‘The One With The Evil Orthodontist,’ Season 1, Episode 20

Synopsis: Rachel hooks up with Barry, her former fiancé, and Chandler goes nuts because a girl won’t return his answering machine messages, which we assure you was a thing in 1995.

No Good?: Barry is a total schmuck, not to mention that he and Rachel have sex in his orthodontic chair, which seems unhygienic. Meanwhile, Chandler’s obsessive tendencies are decidedly off-putting.

The Possible Silver Lining: “I don’t really understand why people don’t like this episode, because I do think it shows the complicatedness of relationships,” says Dunn. “I mean, Rachel was on the verge of marrying someone, and all we see prior to that episode is her part of the story — it shows more depth to her character.”

Plus, Chandler’s desperate answering machine-based politics captured the needy zeitgeist of the 1990s. Or as Dunn puts it, “For me, having lived at that time, it takes me back.”

‘The One With Phoebe’s Dad,’ Season 2, Episode 9

Synopsis: This Christmas episode mostly takes place inside of a taxi, as Phoebe, accompanied by Joey and Chandler, tracks down her estranged father’s address but can’t bring herself to get out of the car.

No Good?: Fans weren’t thrilled with the intensely cramped nature of the episode.

The Possible Silver Lining: Dunn points out that it’s fun to see Phoebe, Joey and Chandler in a storyline together because “that’s not a trio that typically hung out. It would either be Joey and Rachel or Joey and Phoebe.” Not to mention, there’s the bit where the “little tiny dog is trying to attack them in the car, and they try to feed it with a terrible sandwich – the only unbelievable part is that Joey had a crappy sandwich with him. Like, he would normally have a good sandwich.”

Miller is also a fan of the final scene: “At the end when the guys come back with all the Christmas presents from the gas station. That’s funny.”

‘The One That Could Have Been,’ Season 6, Episodes 15 and 16

Synopsis: A controversial two-partner set in an alternate universe where the Friends gang chose a path not taken — like, Ross is still married to Carol, Joey is still on Days of Our Lives and Phoebe has a high-pressure stock market job.

No Good?: Monica’s storyline is just an excuse for more cheap fat jokes, and Chandler is writing for the New Yorker? Really? Also, Phoebe’s (and, to an extent, Chandler's) entire alternate life is created via a throwaway line at the beginning of the episode rather than playing off established canon.

The Possible Silver Lining: “I think it kind of works,” notes Miller. “And that’s because Lisa Kudrow just nails it, the way that she saves the day in so many episodes. Also, interestingly, Rachel’s Jewishness, which they never acknowledge, is played up very stereotypically hard in both of those episodes.”

Dunn observes that it did fulfill a kind of cultural curiosity at the time: “We had five-and-a-half seasons with these characters. And even though there wasn't the same kind of online discussion of ‘What if…?’ there still was fan discussion of ‘What if…?’ The non-redeeming quality is, why do we need to have ‘fat Monica’ and just make fun of her?”

‘The One With Phoebe’s Ex-Partner,’ Season 3, Episode 14

Synopsis: Phoebe randomly has an old musical partner she never mentioned who wants to make some money off of “Smelly Cat.” Chandler starts dating one of Joey’s exes, played by Twin Peaks’ Sherilyn Fenn.

No Good?: Bizarrely, we learn that Joey and Ginger broke up because Joey somehow threw her artificial leg in a fire, then ran away. Chandler then gets super-weirded out by the leg situation until she ultimately breaks up with him because of his superfluous third nipple.

The Possible Silver Lining: “The singing partner part I enjoyed,” Dunn admits, “in part because it told us more about Phoebe’s past with people. Whenever we learned more about Phoebe’s past, it was always kind of fascinating.”

As for the Chandler of it all: “The fact that Chandler then has the issue with her having one leg, that’s the most cringy part to me.” But ultimately, “the episode addresses that — they’re playing something despicable for a laugh. But they’re not taking away the fact that it’s despicable.”

Miller thinks the leg-burning premise was “pretty dark” even for Friends, speculating that it may have gone over better with the show’s huge U.K. fanbase: “They like to go macabre.”

‘The One Where Joey Dates Rachel,’ Season 8, Episode 12

Synopsis: This episode is part of a long arc that tried to revive a Ross and Rachel-type romance narrative, but between Rachel and a serial philanderer who thought potpourri was a snack food.

No Good?: It didn’t work. At all.

The Possible Silver Lining: Miller stresses that this was a mostly terrible creative decision: “It’s just like, ‘Oh, why?! These people are not supposed to be together. Why are you trying to shove this down our throats?’”

But she also identifies one redeeming element in this sea of awfulness — Matt LeBlanc’s performance. “Matt LeBlanc didn’t get a lot of opportunities to show any kind of range. He’s just sort of a dopey goofball. Even when he’s, like, 40 on that show, he’s still like a child inside. But that was the only arc I can think of that allowed him to show any kind of emotional depth, and it’s poignant.”

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