Friends: The Worst Episode From Every Season
4. Season Seven: The One With Chandler's Dad
The single most infamous Friends episode, The One With Chandler's Dad hasn't just aged poorly - it was already deplorable even when it aired in 2001. The "product of its time" argument might somehow work for certain fans, but it's not nearly enough to justify how ugly and offensive the episode really is.
In it, Chandler and Monica travel to Las Vegas to invite Chandler's estranged father to their wedding. It turns out his dad is actually a trans woman going by the name Helena Handbasket, a lifestyle choice that Chandler treats as utterly embarrassing, and the show itself turns into one, big punchline to a joke no one made.
The episode doesn't stop there, though, instead doubling down on its comments about sexuality by having Joey debate whether men can feel masculine in women's underwear. It's about as funny as it sounds.
This, added to the cringe-inducing portrayal of Chandler's transgender father and an uncomfortably unfunny sublot following Ross and Rachel as they try to flirt their way out of a speeding ticket make The One With Chandler's Dad an absolute disaster, and one best left avoided in future.