Of all six of our favorite friends, only Phoebe Buffay managed to keep her close pals out of her love life. Yes, that means we’re ignoring her pool-table fling with Ross from “The One With the Flashback.†Dating outside the Friends group meant that Phoebe encountered a few more colorful characters than Monica and Rachel (Fun Bobby is no Not-Actually-Gay Ice-Dancer Ex-Husband) did, and God, just way, way more famous people than we remembered. While we all know who the best Mr. Buffay was (helloooo, Mike Hannigan), how did her other beaux stack up?
15. Jim (James LeGros)
This children’s erotica novelist is a human double-entendre, but the flighty Phoebe doesn’t immediately realize how truly gross this dude is. Somewhere in the Friendsverse, he is off playing mah-jongg with the creepy restaurateur whom wants Monica to slice those tomatoes up real nice.
14. Parker (Alec Baldwin)
Even with her suicidal mother, her absentee dad, her surprise biological mother, her horrible twin sister, and the deceased pimp she used to live with, Phoebe manages to always see the bright side of life. So when Parker’s unrelenting cheeriness drives even Phoebe up a wall, you know the man is happier than a healthy person should ever be. The woman who once mugged Ross needs a dude with a little edge.
13. Jake (Troy Norton)
A.k.a. the Guy Who Wore Women’s Underwear. Jake might have been a great guy, but all we ever learn about him is his predilection for Victoria’s Secret. At least Robert played basketball.
12. Robert (Markus Flanagan)
A.k.a.: The Guy Who Didn’t Wear Underwear. This sporty dude let it all hang out in Central Perk until finally Gunther told him to put it away. Phoebe must have told him the same thing.
11. Duncan Sullivan (Steve Zahn)
Phoebe married Canadian Ice-Dancer Duncan to keep him in the country and loved him despite the little problem that he was gay. But: twist! He wasn’t gay, and he returned to ask Phoebs for a divorce so he could marry some other lady. If you can’t figure out you like chicks while getting a massage from a beautifully dippy and loyal blonde, then honestly, we don’t need you.
10. Malcolm (David Arquette)
The first time Phoebe dated a guy who was obsessed with her sister; the man was a verified stalker. An Ursula fixation should speak volumes about a dude’s mental state — she is the evil twin, after all —so good-bye to bad rubbish. And Monica agrees.
9. Eric (Sean Penn)
Oscar winner and noted funny guy Sean Penn guest-starred as the fiancé whom Phoebe’s twin sister’s was deceiving. When Phoebe revealed her sister wasn’t a teacher and hadn’t spent time in the Peace Corps, she found herself with a new admirer … who kind of hated her very face. It’s not that much as a shame, as watching Penn guest on a sitcom was just eerie, but not picking up Ursula’s castoffs was a lesson our girl should have learned by now.
8. Roger (Fisher Stevens)
Everyone loved this psychiatrist, who was able to cut right to the heart of any Friend’s problem. The problem? He hated the gang. The show isn’t called Phoebe All Alone by Herself, so Roger had to go.
7. Ryan (Charlie Sheen)
By all rights, Ryan should probably be higher up on this list. He was dashing in his naval uniform and refused to let Pheobe’s case of the chicken pox come between the one night they had to share. But then he had to go and be played by Charlie Sheen. Can’t come back from a blow like that.
6. Sergei (Jim Pirri)
Ah, this handsome diplomat only had one real issue: a complete inability to communicate in English, save a few nouns. Finding each other outside the U.N. while Phoebe gave away free massage was the ultimate meet-cute, but it turns out that touch isn’t the only language. If they could have built a relationship on “plate†alone, it surely would have been one for the ages.
5. Gary (Michael Rapaport)
Phoebe met this NYPD officer after finding and using his badge. He was nice enough to let her off, but not nice enough not to shoot a bird for chirping after the pair moved in together. That literally will not fly. Homegirl’s a vegetarian, for God’s sake.
4. Rob Donnen (Chris Isaak)
Rob was a sweet guy who asked Phoebe to play music for children. Aww, right? But the singer of “Smelly Cat†dropped some hard truths on the kids and found herself unwelcome at the public library. There’s a slight chance Pheebs might have actually messed this one up, but hey, kids gotta learn sometime.
3. Fireman Vince (Matt Battaglia)/ Kindergarten Teacher Jason (Robert Gant)
Phoebe dated these seemingly opposite dudes simultaneously, only to find out her hunk was sensitive and her sweetheart was ripped. Life is rough. The guys freaked out (Jason because she had slept with Vince, and Vince because she had had an open flame in a wooded area), and she was left alone. Ultimately, they just shouldn’t have made her choose. That would have been way more watchable than Sister Wives.
2. David (Hank Azaria)
This nervous, earnest scientist seemed like he could be Phoebe’s one true love — but he left her to do science-y things in Minsk. By the time he returned for good, she had met Mike. David learned a hard lesson that many fellow street kids and at least one cop had to learn: Never turn your back on Phoebe Buffay.
1. Mike Hannigan (Paul Rudd)
Even if Mike didn’t end up being Phoebe’s husband, even if he didn’t declare in his vows that he loved her because she was so “wonderfully weird,†even if he wasn’t a pianist to her guitar player and the Crap Bag to her Princess Consuela Banana Hammock, Mike Hannigan would top this list. Because he’s played charming, ageless wonder-human Paul Rudd. But all that other stuff helps, too.
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