The 25 best episode of 'The Larry Sanders Show,' ranked

This is a very ‘90s episode, not just because it prominently involves Bobcat Goldthwait. It specifically riffs on an appearance of Bobcat’s on The Tonight Show with Jay Leno. At the time, it was probably interesting for people to see Goldthwait out of character. It’s still a fun episode, but almost 30 years later, it doesn’t pack quite the same punch.

Garry Shandling was great on The Larry Sanders Show, and Larry is a great character. However, the best character and performance on the show probably belongs to Jeffrey Tambor as Hank Kingsley. “The Grand Opening” focuses on Hank’s attempt to finally open his revolving restaurant, the “Look-a-Round Café,” which doesn’t go well.

The second season of The Larry Sanders Show ended with Larry unsure about his future after his network was sold. This led to a third-season premiere that sees Larry in Montana trying to figure out his future. The behind-the-scenes machinations of showbiz are what the show did best, and we get a lot of that here.

Hank’s first assistant, Darlene, was defined by the men in the office lusting after her, including Larry. His second assistant, Brian, is played by Scott Thompson, and like Thompson, he is gay. In the world of The Larry Sanders Show, this is a cause for tumult that can be cringe. Larry’s story in this episode about him being mad at Dana Carvey’s impression of him is also really good.

Larry is a talk show host, but he has to diversify. The network wants him to put a sitcom together, and he begins working on one with Chris Elliott. Of course, there are conflicts between Larry’s vision and the network's. These episodes are really only for people who like showbiz commentary, but we’re fans.

A job is a job, even if it seems like an awesome job. Larry is also not the kind of guy to be happy. Though this is an episode from the second season of The Larry Sanders Show, he’s already been on the air in the world of the show for a while. It’s only natural they did an episode where Larry’s interests drift elsewhere.

The story of Artie trying to find a nice pen that Larry gifted him is totally fine, but it’s the other storyline that pops from this episode. With Larry’s show ending, Phil surreptitiously gets a deal to do a pilot for a sitcom with the network, so he quits (underlying pretenses) and leaves the show in the lurch. Phil proceeds to have a nightmare experience with his pilot, which quickly becomes a Dave Chappelle deal that has nothing to do with his original idea. Anybody who has ever had a creative project gets away from them can relate.

This is the earliest episode on this list, the fourth episode overall. It’s also the second appearance on this list from Dana Carvey. Carvey, a friend of Larry’s, steps in as Larry’s guest host, which leads to Carvey getting an offer from CBS. This leads to a rift between the friends, which the show mines laughs and pathos from.

Once again, Larry is asked to do work outside of his own show, as he has to find a host for another late-night talk show. This is, oddly, another appearance from Bobcat Goldthwait on this list. Hey, it was comedy in the ‘90s. There’s also an appearance from David Letterman, which is cool.

The Larry Sanders Show was willing to get really dark. Take, for example, “I Buried Sid,” one of the show's final episodes. Sid, the cue card guy, had always had a small role on the show, and in this episode, he commits suicıde. Hank fears his harsh criticism of Sid pushed him to the act, and Hank is not the kind of person who can handle that. As we said, it’s dark.

Hank converts to Judaism in this episode, but in true Hank fashion, he does it in the most self-serving way. Doing a comedy episode like this could be tricky to handle, but The Larry Sanders Show really manages to thread the needle.

Jeff Goldblum is one of those distinct personalities that always brings a certain energy to any appearance. Even better when he’s playing up his persona in Larry Sanders fashion. Goldblum is a friend of Larry within the context of the show, but in this episode, Larry is pressured to get Goldblum on his show, much to his consternation.

Showbiz is a delicate balance sometimes. Take, for example, “Doubt of the Benefit.” Larry doesn’t want to host a charity benefit because he’s feeling stretched too thin. However, Larry becomes worried that Rob Reiner has canceled on him because he didn’t host his benefit. Thus, the dance begins as Larry tries to get Rob on his show without having to broach the awkwardness of the situation.

Even if you haven’t seen The Larry Sanders Show, you may have heard people yell “Hey now!” out and about. That’s Hank’s catchphrase, which he uses constantly. The season-one finale is about Larry growing tired of how often Hank is saying, “Hey now!” It’s an early exploration of the dynamic between Larry and Hank.

Celebrity roasts may seem fun on paper, but that often isn’t the case in reality. Larry knows this, but he begrudgingly accepts being the celebrity getting roasted. It’s a brutal evening for everybody involved, especially Larry. The cringe comedy of “The Roast” is as high as any episode of the show. It might make some viewers uncomfortable, but it’s really funny if you’re on its wavelength.

During the third season, both Larry and Hank’s lives fall apart. Larry ends up addicted to painkillers, and in the season finale, he gets some unexpected help for his addiction. That help comes from Roseanne. While Roseanne is a complicated figure these days, she’s quite good in this episode.

The Larry Sanders Show doesn’t seem to have the kindest view of agents, which is evident in this episode. Larry leaves his old agent for the up-and-coming Stevie Grant. Stevie is aggressive, ruthless, and a cokehead. He also gets results for Larry. Stevie, by the way, is played by Bob Odenkirk. He showed he had acting chops well before he stepped into the shoes of Saul Goodman.

Do you know a recurring character on The Larry Sanders Show who did a good acting job? Jon Stewart. Sure, he was basically playing himself, but Stewart is a key figure in the show over its run, especially toward the end of the show. The sixth season opens with Larry feeling the pressure from the network because Stewart did a good job as a guest host. It’s some of the best acting Stewart has ever done.

Well, you can guess what this episode is about. You also likely remember it if you’ve seen it. What else can we say? The writers discover a sex tape Hank made. Everybody working on the show ends up watching it. Things get awkward. It’s well-crafted television.

Hank is one of the quintessential showbiz hacks of television. He’s desperate for attention and adoration. In this episode, he finally gets a chance to guest host the show. This may be Tambor’s best episode in the run of the series. Hank gets his chance to shine, and naturally, his ego gets in the way.

There are a handful of frenetic episodes of The Larry Sanders Show. It’s about the production of a TV program, after all. Things are often hectic. Here, Larry and the staff are doing their best to put episodes together, but Larry is also doing everything he can to make sure his friend Jeff Cesario can do a standup set after he’s been bumped multiple times.

Surprisingly, we’ve made it this far before really delving into Artie, played by Rip Torn. Torn is fantastic on this show, and Artie could easily be considered the best character. He has his faults, but when you need something done, you know Artie will do it — likely with a lot of yelling, swearing, and some threats of violence. This episode lets us spend some time with Artie as he considers leaving the show due to Larry’s behavior. It’s a tour de force for Torn.

In 1997, TV Guide declared this the 39th-best episode of television. That’s high praise. Larry is dealing with trying to keep Stewart from taking his job, but he’s also trying to parse his friendship with David Duchovny, who he thinks might have a crush on him. Of all the celebrities as themselves on the show, Duchovny probably stands out the most. This episode is a big reason why.

The stuff where Larry hangs out with his brother is good, but what really matters is what’s happening on Larry’s show while Stewart is guest-hosting. Larry is at the end of his run, so Hank is desperate to try and get in Stewart’s good graces so that he can stay on the show as his sidekick. Stewart, meanwhile, is trying to remake the show and make it edgier. This is exemplified by a sketch where Hank plays, well, if you look at the episode title, you can probably figure out who he plays.

It’s nice to go out with a bang. The Larry Sanders Show ended its run with its best episode. Yes, this is the series finale. They shove in a ton of celebrities, and they don’t all hit. Jim Carrey does, for sure. Sean Penn is less so. All in all, it’s a showcase for everything that made the show so good. Naturally, it ends with Larry, Hank, and Artie arguing, reminiscing, and trying to come to terms with their emotions. There was no other way The Larry Sanders Show could end.