Photo: HBO

In 5 To Watch, five writers from The A.V. Club look at the latest streaming TV arrivals, each making the case for a favored episode. The reasons for their picks might differ, but they can all agree that each episode is a must-watch. In this installment: The Larry Sanders Show, which will be available for streaming on HBO Go on Friday, September 23.

HBO’s sublime Larry Sanders Show managed to look both forward and backward at television history. Not only did it feature a conceited man at the center of his own show-within-a-show, like Jack Benny and Dick Van Dyke’s series had years before, but it also preceded the sharp, caustic backstage looks at showbiz subsequently seen in 30 Rock and Sports Night. Larry Sanders landed somewhere between those two extremes, and then took a turn for the jugular: an always-funny series that poked vicious fun at late-night Hollywood lunacy, while crafting some kind of actual relationships between people that seemed to be addicted to artifice.

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Soon after Garry Shandling died earlier this year at the age of 66, HBO Go announced that Larry Sanders would finally be available for streaming. To help kick off inevitable future binge-watchers, five A.V. Club writers offer their favorite places to dive into the darkly funny backstage world of Larry Sanders; starting with Jeffrey Tambor’s Hank Kingsley, apparently, is never a bad idea. (For more, check out this TV Club 10.)

1. Erik’s pick: “Hank’s Contract” (season one, episode seven)

Jeffrey Tambor started losing his hair in high school. In a Fresh Air interview ahead of Transparent’s second season, the actor describes the experience, explaining that it led him to find inspiration in characters like Mel Cooley, the chrome­-domed fussbudget and office punching bag played by Richard Deacon on The Dick Van Dyke Show. As Larry Sanders sidekick, “Hey now!” Hank Kingsley, Tambor is like Mel times a thousand, all of the cruel jibes and professional jealousies warping him into the petty, impulsive, lecherous oaf who explodes on his boss in the comic centerpiece of “Hank’s Contract.” That scene, culminating in a poorly covered instance of speakerphone eavesdropping, contains one of the finest sitcom jokes ever written, involving a chipped tooth, a bathroom urinal, and Garry Shandling’s evident amusement at the line. For all “Hank’s Contract” does to paint Hank as a laughingstock who couldn’t negotiate his way out of a wet novelty­-sized gift box, his necessity to this world is the thrust of the episode. Special guest star Robin Williams jokingly suggests that Hank would be a perfect foil “for anyone,” but the mixture of self­-loathing and self-­satisfaction on display in “Hank’s Contract” proves he’s right at home on The Larry Sanders Show—the HBO series and the talk show­ within ­the series.

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2. Molly’s pick: “Out Of The Loop” (season one, episode eight)

For as groundbreaking as The Larry Sanders Show was, it was at its heart a workplace comedy. It just happened to be in a workplace where celebrities were a regular presence, and it’s told largely from the perspective of the boss, a neurotic narcissist who has an onscreen affability but would have been horrendous to work for. “Out Of The Loop” is an excellent reminder of that basic premise, even if Peter Falk doesn’t ever come by my office. Larry decides that he should be more involved in the lives of his underlings, giving them romantic advice and acting as a mentor. But Larry’s desire is more about inflating his own sense of self-importance instead of actually helping people. So when his writers and employees actually take him up on his offer to assist, Larry figures out that he’s entirely in over his head, and he wants no part of the meddling he’s gotten himself into. There’s two sides to Larry’s conundrum: He doesn’t actually care about his staff members, which fits in with his general narcissism. But to be fair to Larry, those staff members have basic social deficiencies themselves. For example, Hank can’t even get his fan newsletter—Hank’s Thoughts—written without problems. While dictating it, he spies Jerry (Jeremy Piven) banging a co-worker in the parking lot. Hank’s secretary dutifully continues to write down Hank’s stream of consciousness about the tryst: “I am telling you, nothing beats that missionary position!”

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3. Sean’s pick: “Larry’s Partner” (season two, episode 10)

On any other series, the “alcoholic seeking redemption” trope would have made for a Very Special Episode, full of tearful arguments, a rock bottom followed by last-minute reprieve, and ending with a solemn, “If you or someone you know…” PSA. But Larry Sanders typically treated its characters’ very real personal problems—divorce, addiction, depression—as little more than a whetstone against which its characters could create sharper insults. So when Eric Bogosian turns up as Stan, Larry’s burnout, estranged former comedy partner, the humor remains typically mordant throughout, even as the episode hits some expected beats. Stan’s a bitter, fast-talking mess, and it’s Larry’s guilt over his own success that leads him to add Stan to the show’s writing staff, despite every signal that it will be a disaster. That Stan will inevitably backslide and blame Larry is similarly obvious, while the whole thing culminates in an (surprising, for this show) emotional scene in which Larry, the king of avoiding confrontation, finally tells Stan off. And still, “Larry’s Partner” sidesteps what could have been a clichéd story to become one of the series’ darkest, most darkly funny half hours—even managing to turn Stan’s attempted suicide into a punchline—thanks to its refusal to betray the show’s core commitment to portraying a group of incredibly self-involved people who have no idea how to behave like humans when they’re not on camera. Also, it has Artie barking about hanging around the bathroom “like a crapper gargoyle.”

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4. Gwen’s pick: “Hank’s Sex Tape” (season four, episode seven)

For all our love for Hank Kingsley, there is no darker and more embarrassing moment for the “Hey now!” guy than season four’s “Hank’s Sex Tape.” After stoned writers Jon (Jon Favreau) and Phil (Wallace Langham) find a video called “Hank’s Birthday” in his office, they discover it’s actually a tape of Hank in the most awkward three-way ever put on videotape, which quickly goes viral. The one-liners from the tape alone sell the episode (“Mary Ann’s being mean to me, Professor,” “The snake doesn’t like Artie,” “You need to wash your mouth out… with Hank!”) But in typical Larry Sanders fashion, a surprising ribbon of sentimentality shows up. Hank may get kicked around (frequently) as the Sanders co-host, but Artie is still going to hunt down every last copy of that tape for him, and Larry is going to let Hank’s potential sponsor watch the show in his office, ultimately clinching the gig. Yes, they’re also saving the show, but when it comes right down to it, the Sanders players constitute a family. A fucked-up, frequently mean, dysfunctional family that understands that sex is not wrong when it’s performed by two or more consenting adults.

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5. Alex’s pick: “Putting The ‘Gay’ Back In Litigation” (season six, episode 10)

It wasn’t just Larry and Hank who were staring into the void of an existential crisis during The Larry Sanders Show’s final episodes, as the show within the show coming to an end forced them to reckon with the prospect of life after late night. The rest of the staff was facing an uncertain future as well, and it’s that impending deadline that helps trigger the title lawsuit of “Putting The ‘Gay’ Back In Litigation.” Brian (Scott Thompson), having endured the homophonic taunts of writers’-room asshole Phil for years, threatens to sue the show for sexual harassment. The two eventually end up hunkered down together during one of the final shows, and as Phil drinks Jagermeister and opens his narcissistic heart to Brian, the true source of Phil’s anti-gay attitude becomes clear—the two begin passionately making out. It’s a great reversal of a long-simmering antagonism. But Hank’s and Larry’s spiraling continues unabated, as Hank’s efforts to make Larry a farewell tape of celebrity well-wishers is threatened by his own stupidity, and Larry almost torpedoes his burgeoning relationship with Illeana Douglas by acknowledging he could only be with someone he considers a good guest. It’s that push and pull between the seemingly critical legal situation, yet everyone remaining wrapped up in their own petty crap, that highlights the series’ perpetual tightrope walk of comedy and discomfort.

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