Seinfeld has been off the air for 20 years today. There’s plenty to say about this show about nothing, but let’s focus on the show’s best character, Elaine Benes, and the bizarre, baffling, sometimes-horrible boyfriends she was subjected to in the course of nine seasons. Here’s an authoritative, scientific ranking of her most memorable or otherwise significant love interests, from worst to best, from the “bad breaker-uppers” to the “sponge-worthy.” At the very least, it’s a list that’s bound to make you feel better about your personal life (or dating in New York City).
29. Phil Totola
“He took it out.”
Phil is a sexual harasser, so let’s get him out of the way. Jerry sets Elaine up with Phil in season 5, and they end up having a fantastic date, until he takes it out. He takes it out. He takes. It out. The guy who takes it out is not getting higher than last place on this list.
28. Owen March
“These pretzels are making me thirsty!”
This episode, “The Alternate Side,” is better known as one in which Kramer gets a line in a Woody Allen movie. So perhaps Elaine’s strange relationship with Owen, a senior citizen at 66, can be explained as some kind of “Manhattan” reference. He has a stroke before she can break up with him, and there’s an uncomfortable moment where he’s incapacitated after the stroke, on the couch of Jerry’s apartment, and no one knows what to do. Jerry Seinfeld years later said that this stroke plotline made the episode his least-favorite Seinfeld episode ever.
27. Dick
“What the hell do you know about wagons?”
A co-worker of Elaine’s at Pendant Publishing and a recovering alcoholic, he falls off the wagon after Jerry leaves a vodka-and-cranberry next to him at a party, and Dick mistakes it for his cranberry juice. (Elaine accuses Jerry of doing this intentionally.) He’s eventually fired from his job for drinking, and later drunkenly heckles Jerry during one of his comedy sets.
26. Billy
“I think I’m very sponge-worthy.”
Elaine really likes Billy, but, after learning about a sudden shortage of contraceptive sponges, she decides she needs to reevaluate her “entire screening process.” She puts Billy through a rigorous interrogation to decide whether he is “sponge-worthy.” He’s able to convince Elaine that he is, by making a compelling case (“I own a very profitable electronics-distribution firm. I eat well. I exercise!”) and promising to trim his sideburns.
25. Kevin, a.k.a. “Bizarro Jerry”
“He’s reliable. He’s considerate. He’s like your exact opposite.”
Elaine dates Kevin briefly, but they decide to remain friends, like with Jerry, opening a portal into “bizarro” world, one of the show’s many Superman allusions and one of its best episodes. Kevin is everything Jerry’s not: a reader of books, a generous friend, and not obsessed with what Elaine calls “the excruciating minutiae of every single daily event.” But it’s not long before Elaine is exiled from the group (which includes Kramer counterpart “Feldman” and George doppelgänger “Gene”) after her trademark “Get out!” shove injures Kevin.
24. Ed
“They say no one’s ever beaten the Van Wyck, but gentlemen I tell you this: I came as close as anyone ever has.”
Ed, visiting New York from Seattle, inspired Elaine’s “gold-medal run” to the airport, undertaken in a desperate attempt to get him back on a plane, out of her apartment, and out of her life.
23. Fred
“I really don’t see how you could miss a button like that.”
We only see a little of Fred, Elaine’s co-worker at Pendant Publishing, the (very religious) boyfriend who breaks up with Elaine after she sends out a Christmas card with her nipple exposed. Her parting words to Fred: “I have seen the nipple on your soul!”
22. Lloyd Braun
“Name tags, hmm?”
Lloyd, a childhood nemesis of George Costanza’s who appears in several episodes, was a top adviser to David Dinkins during his mayoral re-election campaign … until he passed along Elaine’s idea that everyone in New York City should wear name tags “to make the city friendlier.” The proposal was a disaster, Dinkins lost the race, and Lloyd had a nervous breakdown. (In recovery, he learned about the “Serenity Now” philosophy.) The winner of the election? Rudy Giuliani, who makes a cameo appearance.
21. Ned Isakoff
“Yeah, well, we still got China, and Cuba.”
The only (known) communist boyfriend: he wears “bland, drab, olive-colored clothing” and keeps copies of The Daily Worker at his apartment, and manages to get Kramer and George swept up in his ideology. His relationship with Elaine ends after she “names names” and gets him blacklisted from the Chinese restaurant Hop Sing’s.
20. Joel Rifkin
“Remy Rifkin? Should I get a beret?”
Joel is a good guy, and it wasn’t Elaine’s fault, or Joel’s either, that he happened to share a name with a real-life serial killer, but it kind of doomed the whole relationship. She tries to make it work by forcing him to legally change his name, but they get in a big fight when they can’t decide. (Her suggestions: Ned, Ellis, or Remy.)
19. Todd Gack
“That’s a nice name, Todd Gack. What is that, Dutch?”
Todd Gack manages to date Elaine without actually ever asking her out, by making absurd bets with her (like that Dustin Hoffman was in Star Wars) and losing, meaning that he has to buy her dinner. On their second, and last, date, he surprises Elaine by showing up with his parents.
18. Tony
“It’s a different world when you’re with a cool guy.”
Pretty-boy Tony becomes a hero to George, who starts wearing his baseball cap backwards in his role as “Tony’s sidekick.” But he ultimately leads to Tony’s downfall after a rock-climbing accident, when his beautiful face is mutilated. Elaine tries to prove to Jerry that she wasn’t only dating Tony for his looks, but ends up breaking up with Tony after the bandages come off.
17. Alan
“I found out that he’s a bad breaker-upper.”
Elaine becomes concerned about this one after discovering that he has a number of crazed ex-girlfriends, one of whom stabs him, another who throws hot coffee in his face. She decides she has to end it, and so Alan tells her she has a big head. She laughs it off at first, but then it starts to drive her crazy, too.
16. Dr. Reston
“Elaine, have you been urinating a lot again?”
Elaine goes on a trip to Europe with her domineering psychiatrist, but once back in New York she decides to end the relationship because she thinks he has a mental hold on her. She makes Kramer pretend to be her new boyfriend so she has an excuse to break up with him, but the plan backfires when Dr. Reston befriends Kramer and talks him into recommending that Elaine stay with Dr. Reston.
15. Fred Yerkes
“What am I doing? I’m on a date with this guy because he didn’t remember me? He’s demented, listen to him.”
They meet at a party, but when Elaine bumps into him on the street later, she realizes that he remembers every single detail about that night, except for her. She becomes obsessed with trying to figure out why, and that’s pretty much the basis of their entire (brief) relationship.
14. Simon
“Where I come from, we don’t say ‘What.’ It’s proper to say ‘Pardon.’”
This rude British buffoon is a pretentious snob who bleeds Elaine of cash and patience as soon as he flies in from the U.K. Elaine starts to worry when he implies he has no plans of returning to England, but she’s eventually able to get rid of him.
13. Brett
“You better let somebody love you, let somebody love you, before it’s too late.”
Brett is obsessed with a fictional furniture designer named Karl Farbman and the song “Desperado,” by the Eagles. Elaine hates it and tries make “Witchy Woman” their song instead, but fails. He actually won’t even let her make “Desperado” their song, because it’s all his. Brett dies after Jerry accidentally hits him in the head with an axe.
12. Jimmy
“Jimmy doesn’t like misunderstandings. Jimmy and misunderstandings … kinda clash.”
Jimmy dates Elaine after they meet at the gym. Jimmy’s unusual way of talking in the third-person confuses Elaine into going out on a date with him. Jimmy even gets Elaine to start talking that way too. Jimmy is definitely a doofus, but Jimmy’s a memorable doofus.
11. John Germaine
“I told him you two were pretty hot and heavy.”
Things are going great with John Germaine, a handsome jazz saxophonist who “doesn’t do everything” in bed, until Jerry memorably tells a friend of John’s that he heard the two were “pretty hot and heavy,” sending Elaine into a panic (“I’m trying to get a little squirrel to come over to me here … I don’t want to make any big, sudden movements!”). They finally get to do everything but it leads to his ruin when his fatigued lips can’t grip his saxophone at a crucial jazz showcase for record execs.
10. Jack
“I’m the Wiz, and nobody beats me!”
He’s the Wiz, and nobody beats him (except for the next nine boyfriends on this list.) Elaine is captivated by dreamy Jack, played by Toby Huss, who always seems to have a twinkle in his eye. But Jerry discovers that the reason Elaine is so in love with him is because she remembers him as “The Wiz” in an old TV commercial. They eventually break up when he announces he’s reprising the character. He’s the Wiz!
9. Jerry Seinfeld
“We just wanna take this, and add that.”
Jerry earns his place here as something like Elaine’s original boyfriend, and her most constant companion. We know he and Elaine dated for a while, longer than any other relationships they have in the show, but not much else about their time as a couple. Though they tried to have a friends-with-benefits situation, in a classic scene where they set “ground rules” for such a setup, their friendship is one of the show’s bedrocks, a fun, teasing, but constant presence amid a merry-go-round of suitors.
8. Hal Kitzmiller
“The walking date is a good date. You don’t have to look right at the person.”
The boyfriend with back pain who takes it upon himself to buy Elaine an ergonomic mattress from the Lumbar Yard, which she takes offense to because she thinks it means he’s being presumptive about sleeping with her, but it turns out he’s just a really nice guy!
7. John F. Kennedy, Jr.
“He has got a great butt.”
John John. Okay, so here’s where we take a little leeway. They never actually went on a date and he doesn’t appear onscreen, but he’s one of the more significant, and memorable, love interests because of his role in disqualifying Elaine from “the contest.” Also because it’s John F. Kennedy, Jr. Elaine takes an exercise class with him, and after he asks Elaine’s friend about her, and makes a plan to meet her outside her building that night. But, alas, he’s late, and they don’t meet up. Tragically, he gets together with Marla the virgin instead.
6. Darryl
“So, we’re just a couple of white people?”
Is he black? George mostly keeps repeating, “I really don’t think we’re supposed to be talking about this.” This sets Elaine on a quest to find out whether he is, but the clues are ambiguous, such as when Darryl claims that his parents came to the U.S. from South Africa for “obvious reasons,” and that he calls Elaine and him an “interracial couple.”
5. Jake Jarmel
“So, you heard that I was in a car accident, and then decided to stop off for some Jujyfruit?”
You can’t say this about many of Elaine’s boyfriends, but Jake is pretty perfect and also normal. They meet after Jake feels the fabric of Elaine’s gabardine coat. Unfortunately, but not for us, Elaine messes their relationship up massively and memorably — twice. First, after coming home to find a Jake cooking a romantic dinner for her, she reads her phone messages and is upset to discover that Jake didn’t include an exclamation point when writing down the news that her friend Myra had a baby! He tells Elaine, I’m leaving!! They break up over punctuation.
They get back together, but in a later episode, Elaine is waiting for Jake at a movie theater when she find out that he’s been injured in a car accident. She rushes to the hospital — but not before buying a box of Jujyfruits at the concession stand. He finds out and breaks up with her, again.
4. Aaron
“He’s nice, bit of a close-talker.”
Elaine is head over heels for Aaron, perfectly portrayed by Judge Reinhold, despite his penchant for “close talking.” Elaine becomes less enthusiastic when she discovers that his kindness and affections extend to Jerry’s parents, who he spends days on end with, taking them to the Met, and inviting them to crash a date with Elaine. When the Seinfelds finally leave, Aaron laments that he could have done so much more for them.
3. Bob Cobb
“Ya know, I feel a little funny calling somebody Maestro.”
Bob Cobb, who, according to a Seinfeld fan wiki, is named after the creator of the Cobb salad, is a Leonard Bernstein wannabe and conductor of the Police Benevolence Orchestra who insists on being called “Maestro” at all times, even in the middle of making out with Elaine. They sing opera in his convertible and galavant off to Tuscany, but eventually break up after she ruins a signed poster of his favorite tenor (not Domingo, not Pavarotti … the other guy) by spilling a drink on it. She tries to make it up to him in a later episode, but the same thing happens again.
2. Keith Hernandez
“I’d watch the third-base coach if I were you, because I don’t think he’s waving you in.”
The former New York Mets baseball player, who plays himself, really hits it off with Elaine, in a two-part episode that is actually called, “The Boyfriend.” Things get weird when Keith enters into a bizarre love triangle with Jerry, who starts jostling with Elaine for Keith’s time and attention. But Elaine dumps him when she finds out he’s a smoker.
1. David Puddy
“Yeah that’s right.”
The lovably dumb mechanic, recovering germaphobe, and diehard New Jersey Devils fan is Elaine’s best boyfriend. Their on-again-off-again relationship (he appears in ten episodes) becomes a running joke (George: “How did Puddy get back in the picture?” Elaine: “I needed to move a bureau”) but they’re great when they’re together. (Or at least as great as romantic relationships get on the show, let’s be fair.) He’s got his weird qualities of course, a penchant for high-fiving, his love of Christian rock and Jesus fish, his questionable face-and-body painting, but, in a show full of jerks, he’s not one of them.
