It wasn't all fun and water balloon fights when it came to these supporting characters, though. There were some recurring and even one-off characters that did nothing but grind on all the nerves -- no disrespect to the actors portraying them, of course. Click through to see who we hated the most as you revisit the celebrated comedy, which is now streaming on HBO Max.
The rest of the gang was right to make fun of Parker (Alec Baldwin). As much as Phoebe's own dating history could read like a "Who's Who of Human Crap" -- lookin' at you, Rog -- Parker and all his ultra-sunny takes were much too much, and, yeah, he had to go. Don't let the best door in the world hit you in the rear on the way out, guy.
The hitting thing? Like ... why? Why did this girl Katie (Soleil Moon Frye) feel the need or right to go on about smacking everyone in the arms just to prove she was cute and tiny and ineffectual at hurting people? It was only fun to make fun of Joey for being a wimp for so long.
The runner-up for Miss Oklahoma, Wendy (Selma Blair) was a hot mess, and she knew it. Although Chandler should've probably picked up all the signals she was throwing down earlier than he did, Chandler's always been clueless so we'll have to let it slide. Between all her ham-stealing and adultery, though, Wendy knew exactly what she was doing, and ughh. Stop.
You pretty much can't judge a laboring mom-to-be for anything, but somehow, Doreen (Debi Mazar)'s behavior still crossed that line and became too intolerable to take. Between slinging insults at everyone in the room at any given time and defending her pervy husband for sneaking a peek at Rachel in a delicate state, this was not a pleasant person at all. Nah uh.
Charlie certainly deserves some demerits for hopping right back into his arms as soon as the water was warm, without any warning to Ross (whom she hooked up while still with Joey, but nevermind that). But Dr. Hobart (Greg Kinnear) used his position of academic authority to punish Ross for a personal rift, which is even worse than when Ross decided it was a smartguy move to hook up with a student at his university.
There was something very satisfying to the pop culture world about seeing Brad Pitt guest star on Jennifer Aniston's show because they were tabloid sweethearts at the time for sure, but his character was kinda the worst. Here's a guy who can't keep it together for the length of one freaking meal that he's an unexpected guest at and who also does his former best friend the disservice of ratting on his bad behavior of old in front of his baby mama-to-be. How mature.
He wasn't the only one of Ursula's castaways that Phoebe would take a shine to, but there was almost nothing redeemable about Malcolm (David Arquette). He was dense, obsessive, and duplicitous. As Joey might say, Phoebe sure does pick "some stinkers."
Contrary to Chandler's opinion, Amanda (Jennifer Coolidge) absolutely could not dance, and that was the least worst thing about her. Her utter fakery and intolerable boastfulness made her ripe for the friend removal list, and Monica and Phoebe were right to cut her out of their lives long ago.
As ditzy and materialistic as Rachel was when she first broke things off with Barry, she at least had a sensitive side to speak of. Not so for her little sister Jill (Reese Witherspoon), who was so self-absorbed and unkind that she made a point of trying to seduce Ross just for the sake of making her own flesh and blood sister miserable... remembering that this is the thanks Rachel got for trying to help her sister come out of her stuck-up spoiled girl coma, yeah, it's pretty bad.
She might've been cool enough to watch midnight Ernie Kovacs specials and hang out in a hockey jersey in the living room canoe, but Kathy (Paget Brewster) was a pretty messed up individual in the end. After Chandler accused her of sleeping with her co-star behind his back, she went and did just that because reasons.
The other Green sister to come into the picture was somehow even worse than the rest. Amy (Christina Applegate) was a total scene-stealer, yes, but she was also gnawingly ridiculous, with all her pompous dismissals of literally everything in Rachel's life -- including her daughter, which is, to quote Ross, simply "too far." And the way she bludgeoned Monica's wedding china? Rude doesn't begin to describe it.
This dude was legitimately like a cartoon. Long before Ben Stiller would star alongside Jennifer Aniston in Along Came Polly, he portrayed her veryyyy temporary love interest Tommy, who had quite the attitude problem. Somehow, he only lifted the veil on his intense rage in front of Ross, but once everyone got a good look at the real Tommy -- bursting into hysterics over the group's beloved birds, no less -- his time on the show was mercifully over.
Suzie Moss (Julia Roberts) held a grudge for an offense that happened all the way back in second grade, and it was not OK. After a chance run-in with Chandler, she decided to seduce him into wearing her thong panties so that she could ditch him and steal his clothes, leaving him to wander the chilly streets of New York in his knickers just because of something his 7-year-old self did. What a gal.
No one loved hearing about how wonderful Jean Claude van Damme was than Jean Claude van Damme. It was ... gross, and we have no idea how both Monica and Rachel were so entranced with this pompousness.
There are not one but two terrible appearances by Steve (Jon Lovitz). In the first, the erstwhile restaurant owner got high on the way to Monica's audition for his chef job and wasted her time, precious little remaining money, and energy all the while. Not cool, Steve. Then, years later, he was set up with Rachel on a blind date, and while she didn't seem to remember him from before, she was definitely not impressed by his lack of accomplishments, self-disdain, and openness about his many, many issues.
Phoebe might've started to be charmed by Eddie (Adam Goldberg) at the height of his mania, but everyone else was rightly freaked out. It's not quite clear what's ailing this guy, but it's clear he needed some extensive treatment for all his imagined conversations and paranoia over Chandler's relationships with his ex-girlfriend Tilly and his fish, real and fake. The resulting reactions from his very temporary roomie might've been hilarious, but when he finally got the boot, it was nothing but a relief.
Speaking of loose cannons, Joey's stalker Erica (Brooke Shields) wasn't just a bit bizarre. She was so severely lost in the la la land of fiction that it was a wonder how she managed to function on a day-to-day basis.
It doesn't really matter that he tried to redeem himself in the end, Gavin (Dermot Mulroney) was still an opportunist who tried to sabotage a nursing mother's job status for his own gain. Next.
Eventually, she came around and helped Joey take over her role, but Jessica Lockhart (Susan Sarandon) was a piece of work on the set. She was demanding, dismissive, a full-on diva, and downright violent with her co-star during what was supposed to be a fake slap.
Not only did she deny what happened between her and Rachel, but Melissa (Winona Ryder) then tried to gay-shame the girl by suggesting that she might've molested her in her sleep without her permission. The absolute nerve of this one.
Poor Sophie. Joanna (Alison La Placa) was the kind of boss that would definitely infect your nightmares on a daily basis. And remember how she didn't even hesitate to ruin Rachel's interview for another position in the company? No wonder no one was sad she got run over.
Rachel's next boss Kim Clozzi (Joanna Gleason) wasn't much better. She was so snappy and unapproachable that it made Rachel's job virtually impossible at times. By contrast, Mr. Zellner was a dream.
He might've been generous to his daughters, but Dr. Green (Ron Leibman) seemed to delight in tormenting and then stiffing the waitstaff whenever he went out to eat, to the point that he'd earned a reputation around town for being a rude dude. On top of that, he was also a hypocrite -- telling his daughters horror stories about smoking but still hitting the hallway to have a puff himself, e.g. -- put his kids in the middle of his messy divorce, and made fast enemies with Ross for absolutely no reason.
Whether or not you agree with Ross that he and Rachel were on a break, you have to side with him on the fact that he really had just moved into the apartment when Steve (Willie Garson) came a-knocking with a handout for the handyman. That bill should've been paid by Ugly Naked Guy, no doubt about it.
In another instance of Phoebe going after her sister's exes -- and in this case, she was actually moving in while they were still dating, which is sooo full of nope -- she and Eric (Sean Penn) dated for half a minute, all of which was absolutely terrible to witness.
We're not going to go and cry-shame the guy like Rachel did, but Paul Stevens (Bruce Willis) was still completely irritating with the way he would puff up with all that righteous indignation and then wither away each and every time. He had every right to rat on Ross for dating his daughter, so why didn't he just go and do it if he cared so much? It was all about that drama with that one, as his little mirror display well proved.
You might say "Oh my God" for us including Janice (Maggie Wheeler) here, but, yes, she was problematic, too. Consider the fact that she hooked up with her ex-husband twice while dating Chandler -- not long after she said Chandler seeing someone else would make him "the biggest jerk on the planet," mind you. And then think about when she told Rachel that Ross would ditch her for "little miss new boobs" and go full-on deadbeat dad just because they weren't married. Not a very modern way of thinking, Janice! And let's not forget the time she almost moved in next door to Chandler and Monica just to lean into the awkward tension. Janice was funny and sweet sometimes, but she also had that nails-on-a-chalkboard effect at times, too.