Crazy ‘Seinfeld’ Bosses, Ranked

12 Mr. Tuttle

Played By: Jack Shearer

Who Worked for Him: George

Who He Was: In Season Five’s “The Barber,” George interviews with Sanalac — a rest-stop supply company. Everything seems to be going well when the hiring manager, Mr. Tuttle, says, “I want you to have this job, of course…” But before he can finish his sentence, he’s interrupted by his secretary, leaving George confused as to whether or not he’s being hired. George’s plan to show up at the office while Mr. Tuttle is on vacation backfires when he’s given the “Pensky file” and has no idea what work needs to be done. We don’t see much of Mr. Tuttle in the episode — and admittedly, he wasn’t the funniest or most outrageous boss — but he was still an integral part of a classic George storyline.

11 Harry

Played By: Dave Florek
Who Worked for Him: Kramer

Who He Was: Harry is the extremely lenient owner of H&H Bagels. Kramer returns to H&H after being on strike for 12 years, and Harry still hires him as he needs additional help during the holidays. A few days later, though, Kramer goes on strike once again, picketing outside H&H because Harry won’t give him a day off for Festivus (Frank Costanza’s invented holiday). Yet, even after Kramer sabotages a bagel machine, Harry continues to employ him. It’s only after Kramer drops a piece of gum into the bagel dough and tries to pull it out without anyone noticing that Harry has finally had enough and fires him.

10 Mr. Leland

Played By: J. Patrick McCormack
Who Worked for Him: Kramer (sorta)

Who He Was: Mr. Leland isn’t officially a Seinfeld boss because Kramer doesn’t actually work for him. Kramer merely stumbles into the offices of Brandt-Leland after using their bathroom. Nonetheless, Mr. Leland still reviews Kramer’s work, telling him, “Quite frankly, it stinks!” His brutal honesty and subsequent termination of Kramer is among the most quoted moments in the entire series.

9 Mr. Thomassoulo

Played By: Gordon Jump
Who Worked for Him: George

Who He Was: Mr. Thomassoulo is George’s boss at Play Now, where he mistakes George’s walking cane for him being disabled. George chooses not to correct him when he’s told he will have a private, fully equipped bathroom because of it. When Mr. Thomassoulo discovers George has been lying, however, he’s unable to fire him because they signed a one-year contract. Instead, Mr. Thomassoulo tries to make George’s life a living hell by turning up the heat in his office and bolting the door shut. But George continues to show up with a smile on his face anyway, crawling through the air duct to get into his office. It’s an epically hilarious game of cat-and-mouse.

8 Rick Levitan

Played By: Fred Applegate
Who Worked for Him: George

Who He Was: The slimy, greedy and selfish Rick is a big-time Seinfeld villain who cheats on his wife — and even worse, doesn’t recycle. The scene where George storms into Rick’s office to quit and then arrives at work the next day as if nothing had happened is famously based on a real experience from Larry David’s life. After quitting Saturday Night Live, David realized he’d made a huge mistake. When he got back to his apartment and told the story to his neighbor, Kenny Kramer, he advised him to “just go back Monday morning and pretend the whole thing never happened,” which, like George, he did. 

7 Russell Dalrymple

Played By: Bob Balaban

Who Worked for Him: George and Jerry

Who He Was: Russell is the president of NBC, and a major character in the Season Four arc of the “Jerry” show when Jerry and George pitch him a “show about nothing.” He also catches George staring at his daughter’s cleavage, remarking, “Get a good look, Costanza?” His obsession with Elaine results in him quitting his job and joining Greenpeace in hopes of gaining Elaine’s respect when he returns home. Unfortunately, this plan doesn’t pan out as he falls out of a boat and dies in the middle of a Greenpeace mission.

6 Mr. Wilhelm

Played By: Richard Herd
Who Worked for Him: George

Who He Was: Mr. Wilhelm is George’s supervisor at the Yankees, and reported directly to George Steinbrenner. When he’s on his medication, Mr. Wilhelm seems like a no-nonsense boss who takes his job very seriously. But as we see in certain episodes, he’s capable of assigning entire projects to people without ever realizing that he already did it all on his own. Furthermore, he gets brainwashed by the Sunshine Carpet Cleaners and tells George, “My name is Tanya.” Overall, Mr. Wilhelm’s chaotic energy fit the Yankees storyline perfectly.

5 Mr. Lippman

Played By: Richard Fancy
Who Worked for Him: Elaine

Who He Was: Mr. Lippman is Elaine’s boss at Pendant Publishing. Though he plays the straight man, Richard Fancy’s facial expressions and responses always elevate every punchline. One of the best Mr. Lippman scenes is in Season Three’s “The Red Dot.” After Elaine recommends George for a job, Mr. Lippman fires George for having sex with the cleaning woman. Every moment of that scene is brilliant, and it wouldn’t be the same without Fancy’s fantastic performance.

4 Mr. Pitt

Played By: Ian Abercrombie
Who Worked for Him: Elaine

Who He Was: Elaine’s needy, eccentric and unpredictable boss in Season Six. He assigns her the oddest tasks, including picking out his socks, removing salt from his pretzel sticks and calling into a radio station for a chance to march with the Woody Woodpecker balloon in the Macy’s Thanksgiving Day Parade. He’s also the originator of using a fork and knife to eat a Snickers bar. 

3 Mr. Kruger

Played By: Daniel von Bargen
Who Worked for Him: George

Who He Was: It only takes nine years, but George finally meets his work soulmate when he begins working at Kruger Industrial Smoothing. As George himself exclaims, “This Kruger guy is clueless. I can’t wait to work for him!” Kruger is indeed an incompetent, dim-witted boss. Whether he’s reminiscing with George about “the boombox incident,” writing a $20,000 check to the Human Fund or locking himself out of his office (yet again), Kruger knocks it out of the park every time he appears. 

2 George Steinbrenner

Played By: Larry David
Who Worked for Him: George

Who He Was: Like the aforementioned Mr. Wilhelm, there were all kinds of memorable characters during George’s stint as the assistant to the traveling secretary for the New York Yankees, including George’s secretary Ava. But no one could top the big man himself: George Steinbrenner. Voiced brilliantly by Larry David, his rants are legendary — from going off about calzone, to believing that Babe Ruth was “nothing more than a fat old man with little girl legs.” David called up the real Steinbrenner to shoot a few scenes for the Season Seven episode “The Invitations,” but he was unhappy with his performance and decided not to include it in the show. You can watch the video below and be the judge. I personally prefer the Larry David version:

1 J. Peterman

Played By: John O’Hurley
Who Worked for Him: Elaine

Who He Was: J. Peterman is Elaine’s eccentric boss at the eponymous J. Peterman Catalog, where Elaine writes stupid stories about different articles of clothing like a Norwegian ice fishing vest or a pair of Himalayan walking shoes. At first glance, Peterman seems like a classic romantic leading man — a charming, handsome and stylish individual who can sweep any woman off her feet. But as Elaine spends more time with him, his unpredictability and bizarre stories about his peculiar life experiences obliterate that stereotype. O’Hurley described the character best when he said, “J. Peterman was a legend in his own mind.” He’s certainly a legend in ours, too.