10 episodes that made The Larry Sanders Show one of the best comedies of the ’90s

10 episodes that made The Larry Sanders Show one of the best comedies of the ’90s

With so many new series popping up on streaming services and DVD every day, it gets harder and harder to keep up with new shows, much less the all-time classics. With TV Club 10, we point you toward the 10 episodes that best represent a TV series, classic or modern. If you watch these 10, you’ll have a better idea of what that series was about, without having to watch the whole thing. These are not meant to be the 10 best episodes, but rather the 10 most representative episodes.

As Hollywood basks in the afterglow of the Academy Awards, it’s unnecessary to explain why show business is such a perfect target for satire. Anyone who has sat through the Oscar telecast knows the nearly lethal level of self-importance it exudes, as Hollywood congratulates itself for another successful year of Really Important Work. By this point, it’s a cliché to deride the Oscars (or Emmys, Golden Globes, and sundry other awards shows) as a self-involved circle-jerk.

Many television series have satirized show business, but none more realistically or successfully than HBO’s The Larry Sanders Show, created by and starring Garry Shandling. Thanks to its inspired setting of a late-night talk show, it could draw from the entirety of show business in each episode (film, TV, music, sports, etc.), as a parade of stars came through playing themselves. Its run from August 1992 through May 1998 meant it was also in a perfect position to reflect the decade’s late-night wars. 

Shandling knew the area well. In 1986, he started guest-hosting The Tonight Show for Johnny Carson, and by the early ’90s (after the groundbreaking It’s Garry Shandling’s Show ended), networks were courting Shandling to host a late-night talk show. He was offered the Late Night job before Conan O’Brien was. Letterman wanted Shandling to take over the 12:30 slot once Letterman moved to CBS. Shandling refused them all; in an interview with critic Tom Shales that accompanies the Larry Sanders complete-series DVD, he says he didn’t think he could pull off a show five nights a week. No, if It’s Garry Shandling’s Show had taught the world anything about Shandling, it’s that he thrives on the meta: Instead of hosting a late-night talk show, he’d do a show about hosting one.

The Larry Sanders Show wasn’t like 30 Rock, which almost exclusively stayed backstage at The Girlie Show. Sanders split its time between the set of the talk show (also called The Larry Sanders Show) and the office (or Larry’s house and a few other locations). The two sides were shot differently: The live talk-show parts used video and were shot like a real talk show—so to viewers, it looked indistinguishable from peers like The Tonight Show or The Arsenio Hall Show—but everything else used film. So if Larry were interviewing a guest on the panel for the show, it’d be video. When the show took a commercial break, it switched to film. It went a long way toward making The Larry Sanders Show—the late-night talk show—feel real, along with groan-inducing monologue jokes about the news of the day, trite interviews, and the occasional musical guest.

Shandling nails the role of Larry Sanders, equal parts ego and insecurity, entitled yet spineless. He’s a shallow guy who desperately wants not to be thought of that way. Shandling inhabits the role so well, he makes it look effortless, but The Larry Sanders Show’s biggest assets are two supporting players: Rip Torn as producer Arthur, and Jeffrey Tambor as sidekick Hank Kingsley.

Torn’s career stretches back more than five decades, but it isn’t hyperbolic to suggest that his portrayal of Arthur is his best work. Shandling presumably spoke to other actors for the role, but it’s difficult to imagine anyone doing it better than Torn. Based on Fred De Cordova, Carson’s longtime producer, Artie is the quintessential “guy behind the guy”: Larry is the star, but Artie makes everything work. Artie is the archetype of the showbiz lifer: He’s perfectly in tune with his star, knowing when to push and when to flatter. He deftly glad-hands network executives and the show’s guests, and he treats the show’s staff with a blunt frankness that’s highly quotable. Naturally, Larry takes Artie for granted, which causes the friction that propels several episodes of The Larry Sanders Show.

To oversimplify the character, Hank Kingsley is a buffoon. He’s an inveterate sellout—eager to give his name and likeness to just about anything if it means a paycheck —a womanizer, a comedic hack, and a general jackass. He’s a conniving asshole, but also a hopeless naïf, as trusting and loyal as a dog. As with Torn and Artie, it’s inconceivable that someone besides Tambor could play Hank. As much as he serves as a frequently pathetic straight man to Shandling, Torn, and just about everyone else, Tambor has the opportunity in many episodes to show the real humanity and hurt lurking under Hank’s goofball exterior. Always eager to play ball and take on any demeaning task, he perfectly complements the acerbic, standoffish Larry. 

Torn and Tambor get most of the attention, but The Larry Sanders Show had a wealth of excellent supporting players, such as Penny Johnson as Larry’s assistant, Beverly; Wallace Langham as head writer Phil; Janeane Garofalo as talent booker Paula; Scott Thompson as Hank’s assistant; Bob Odenkirk as Larry’s agent; and many others (including, in later seasons, Sarah Silverman and Mary Lynn Rajskub). Behind the camera, the series featured Judd Apatow as a writer and occasional director, as well as several all-stars on the writing staff, such as Paul Simms (who went on to create NewsRadio), John Riggi (who wrote/produced 30 Rock, The Comeback, and The Bernie Mac Show, among others), Peter Tolan (who wrote for Murphy Brown and later created Rescue Me), Jon Vitti (The Simpsons, King Of The Hill, The Critic, Da Ali G Show), and Drake Sather (a former SNL writer who created Zoolander with Ben Stiller).

For six seasons on HBO, The Larry Sanders Show made some of the best comedy on television, earning two Peabody Awards and three Emmys (one for directing, one for writing, and a much-deserved supporting-actor trophy for Torn), and numerous nominations. It also reflected the times well, particularly the shifting late-night landscape of the ’90s, from the serious but short-lived threat of Arsenio to Conan’s rocky start to Letterman vs. Leno, along with nods to late-night failures like Chevy Chase and Pat Sajak. Now, the monologues serve as time capsules of the ’90s (the L.A. riots! Bill Clinton’s promiscuity! Michael Jackson’s perversions!), but the show remains funny 15 years after it went off the air. Shandling, Torn, and Tambor could carry it with their performances alone, but snappy writing, smart direction, and an excellent supporting cast mean they don’t have to.

Here are 10 episodes that show The Larry Sanders Show at its peak.

“The Hey Now Episode” (season one, episode 13): Although it aired as the final episode of season one, “Hey Now” was the first episode The Larry Sanders Show shot. As Shandling explains in the DVD interview, he thought “the tone was a little heavy” for a pilot, so the series began with “What Have You Done For Me Lately?” But “Hey Now” feels like an introductory episode, as all the primary characters are introduced and central relationships established. Larry considers replacing Hank, because he’s seemingly too distracted by his myriad endorsement deals and outside appearances to bring his A-game to the set—or even stay awake. As Larry points out, Hank actually fell asleep during a segment once. “Of course he was asleep—he’s a fucking moron,” Artie retorts. Most of the time, Hank seems out of place on The Larry Sanders Show, to the point that it strains credibility that the show would keep him around, until he turns out to be exactly what Larry needs. Here, he bails Larry out of an incredibly tedious interview; in “What Have You Done For Me Lately,” he saves the day when the network demands live commercials on the show. Hank may seem like a fool, but he’s a necessary foil for Larry.

“The Spiders Episode” (season one, episode 3): In the annals of late-night history, no moment looms larger than Ed Ames’ famous tomahawk throw on The Tonight Show in 1965. Such spontaneity is rare in the heavily rehearsed world of late night, so such moments tend to live on as defining ones. Showbiz history hangs over “Spiders,” from the Ames clip to a supporting role by Carol Burnett (for which she earned an Emmy nomination), and the way Larry gets his own Ames moment when a segment with the Arachnophobia spiders goes haywire. As much as The Larry Sanders Show drew laughs from its smart dialogue and great characters, “Spiders” proves the show could do physical comedy too.

“The Party” (season one, episode 10): Considered one of the best episodes of The Larry Sanders Show, “The Party” is a season-one highlight that ably captures all of the show’s relationships. When Larry’s wife, Jeannie (Megan Gallagher), breaks protocol and invites Artie and his wife—neither marriage would last—over for dinner, office politics cause it to spiral into a big shindig that makes plain the issues in Larry’s marriage (and his discomfort mixing his home life with his personal life). The second half of the episode provides another showcase for Rip Torn, as Artie gets drunk and belligerent on his signature drink, the Salty Dog.

“The Hankerciser 200” (season two, episode six): Some of the best episodes of The Larry Sanders Show are Hank-driven, because the character offers so much possibility, and Tambor plays him so excellently. Hank’s Krusty The Clown-esque shilling is a frequent theme; it’s right there in episode one, when the network doesn’t want Hank to do the live commercial because his “saturation level is too high.” “The Hankerciser 200” nicely mixes a story about Hank endorsing yet another crappy (and dangerous) product with another about Arthur trying to show a class he teaches at UCLA a “typical day” at The Larry Sanders Show. Only that “day” stretches into several because he keeps trying to hide the madness of what happens there. But the episode shines by showing the many flavors of Hank Kingsley: pitching, glad-handing, angry, desperate, and shameless.  

“Life Behind Larry” (season two, episode seven): One of the episodes most heavily informed by the real world, “Life Behind Larry” concerns the search for a host for the 12:30 show after Larry Sanders. At the time, Letterman was about to start at CBS, and Leno on NBC, with Arsenio still a threat in syndication, but there was nothing happening at 12:30. (“Life Behind Larry” aired in July of 1993, two months before Conan O’Brien made his Late Night debut.) Larry wants something edgier at 12:30, so he suggests Bobcat Goldthwait, whose ideas for a show couldn’t be more at odds with the network’s. Larry ends up competing with Letterman, both to find a host for 12:30 and for a statue at the American Television Awards, and the whole thing plays out in typically ridiculous fashion, but with many details reflecting what was happening in late-night at that time. 

“Off Camera” (season two, episode 16): There may be no older sitcom trope: Everything has to go right when an important person shows up, but nothing does. In the best “bunch of crazy crap happens” episode of The Larry Sanders Show, a reporter from Entertainment Weekly is doing a story on the show, but chaos reigns as Artie bangs a guest, Phil gets drunk, Hank’s assistant Darlene (Linda Doucett) brings a stray dog to the office, and John Ritter and Gene Siskel get into a fistfight. (It’s also an episode of untimely deaths, as Ritter, Siskel, and musical guest Warren Zevon have all died.) Artie has to keep all of it from Larry, because that’s his job, but even a maestro like Arthur can’t do it all.

“Next Stop… Bottom” (season three, episode 15): “The Hankerciser 200” showed the many flavors of Hank, but “Next Stop… Bottom” finds him in a deep pit of despair after the dissolution of his short-lived marriage to a much younger woman with daddy issues. (Shockingly, marrying a woman he just met on air didn’t end well.) Artie describes Hank’s “ol’ spiritual tailspin” perfectly: “He’s hit bottom and broke through to another bottom I know nothing about.” After the guests, at least one crew member, and (in a thoroughly uncomfortable scene) Darlene rebuff his desperate advances, Hank holes up in a hotel with a succession of prostitutes, boozing and banging away his pain. The only man who can pull him out of it is Arthur (himself a veteran of a few divorces) and a cigarette lighter that looks like a gun.

“Arthur After Hours” (season four, episode three): Another favorite theme of The Larry Sanders Show is how much Larry relies on Arthur while simultaneously taking him for granted. Artie is a consummate professional, an old-school showbiz guy who has an almost magical ability to manage high-maintenance creative types while fending off incursions from a network with questionable loyalty. In “Arthur After Hours,” we see Rip Torn manage a punishing gauntlet of problems, only to be rewarded with Larry scapegoating Arthur for his own mistake. That leads to one of Artie’s apparently routine dark nights of the soul, when he gets liquored up, leaves Larry angry voicemails, and quits the show—then returns to normal once morning arrives. “Arthur After Hours” nicely showcases the talents of Rip Torn, who conveys the loneliness of his job and the deep hurt he feels. Torn makes The Larry Sanders Show, and “Arthur After Hours” gives him room to flex his considerable skill.

“Everybody Loves Larry” (season five, episode one): Toward the end of his reign on The Tonight Show, Johnny Carson started slipping in the ratings, losing ground to hip upstart Arsenio Hall, and NBC began to subtly push Carson out the door. As Larry tells Arthur in “Everybody Loves Larry,” Jay Leno was made permanent guest host, then he started to get better guests than Johnny, until Carson apparently got the message. The same thing happens at the start of season five of The Larry Sanders Show, as the network begins grooming Jon Stewart to replace Larry—but without NBC’s gentle touch. When Stewart comes on to guest host while Larry’s on vacation, network executives assure Arthur they just want to “make sure we have a backup quarterback,” but Stewart’s contract with David Letterman’s production company is up soon, and… well. Behind-the-scenes maneuvering propels “Everybody Loves Larry,” as Larry tries to unload a bunch of crappy guests on Stewart (Sally Struthers! Zsa Zsa Gabor! Charles Nelson Reilly! Jamie Farr!) to make sure the kid doesn’t show up the big man. “Normally, I would do this behind your back, but you’re a good guy,” Larry tells Stewart. But what’s inevitable can’t be evaded.

“Flip” (season six, episode 11): The series finale of The Larry Sanders Show follows exactly how the series finale of the late-night show-within-the-show would play out: with tons of guest stars and tributes. But this being The Larry Sanders Show, the whole thing barely comes together, with Tom Petty fighting with Clint Black, and Bob Odenkirk blowing rails on a conference table. The Larry Sanders Show is rightly hailed as one of the best comedies of the ’90s, but it also had real heart. The episode ends with some genuinely touching moments among Larry, Artie, and Hank, nicely showing what Garry Shandling always said about the characters on The Larry Sanders Show: They love each other. “Flip” makes that plain and offers one of those rare treats in television: a satisfying series finale.

And if you like those, here are 10 more: “Hank’s Contract” (season one, episode seven), “Out Of The Loop” (season one, episode eight), “Hank’s Wedding” (season two, episode 15), “The Grand Opening” (season two, episode 17), “Hank’s Night In The Sun” (season three, episode six), “Arthur’s Crises” (season three, episode 16), “Hank’s Sex Tape” (season four, episode seven), “My Name Is Asher Kingsley” (season five, episode two), “The Roast,” (season five, episode 12), “Putting The ‘Gay’ Back In ‘Litigation’” (season six, episode 10).

Availability: The entire series is available on DVD from Shout! Factory, and individual episodes are available on Amazon Instant. Netflix only offers the first season on DVD.

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