The Larry Sanders Show debuted on HBO in 1992, at a time when the cable network barely had any original series. The only other ongoing programs of note were the horror anthology Tales from the Crypt and the sex-laden sitcom Dream On, which was mostly notable for its relentless intercutting of old television clips representing the lead character’s subconscious. Created by Garry Shandling and Dennis Klein (though Peter Tolan also put a sizable stamp on the series), The Larry Sanders Show depicted the backstage tumult at a late night talk show, buffeting the viewer with scathing showbiz satire, with a particular focus on the interweaving and conflicting narcissistic tendencies of practically every person working in the field. It was brilliantly conceived and rendered, boldly redrawing the borders of what a television comedy could be. The awards-giving bodies — especially the Television Academy — simply couldn’t figure out what to do with it.

Only a few years after the Emmys shifted eligibility rules to expand beyond over-the-air broadcast offerings, The Larry Sanders Show became the first cable show to nab a nomination in one of the best series categories. In its six season run, it collected fifty-six total Primetime Emmy nominations. Demonstrating the industry’s reluctance to honor cable series at the time, The Larry Sanders Show lost time and time again, earning only three trophies, one of the great feats of futility in the awards show’s history. The shutout lasted until the fourth season, when Rip Torn won a supporting actor prize for playing Arthur, the grizzled veteran talk show producer. Following that, the show went unrewarded until the episode that was very literally the Academy’s last chance: the series finale, entitled “Flip.”

In keeping with the show’s meta element, the last episode of The Larry Sanders Show was about the last episode of the identically-titled late night series hosted by Larry Sanders (Shandling). Essentially mirroring and condensing to a single show the extended departure of Johnny Carson from The Tonight Show, right down to the imperative to have a musical performer sing goodbye to the retiring host. And Larry signs off while sitting on a stool in front of the stage’s main curtain, just as Carson did. While “Flip” includes a big chunk of the show within the show, the main driver of the episode are the anxious machinations to make the finale of Larry’s run in late night properly memorable. Even on the way out, Larry’s ego, more than anything else, is what’s on the line.

The episode contains the usual array of bruising jokes, but there’s also a notable amount of sentiment laced throughout it. Without ever feeling like it’s crossing over to overly comment on the end of the version of The Larry Sanders Show that bore Shandling’s name as a main creator, “Flip” allows for a sense that the ending of a television program is a jarring dissolution of a large working family, tied together tightly, but temporarily. All these intense relationships click off like an old television tube, leaving only a ghostly dot. Staying true to form, though, the sweetness — and bittersweetness — can always be undercut, as with the fantastically profane tirade Larry’s sidekick, Hang Kingsley (Jeffrey Tambor), unleashes at Larry and Artie as they sit reminiscing after the show has wrapped.

Winning in the directing and writing categories, it’s clear that “Flip” stood for the entirety of the run of The Larry Sanders Show for Emmy voters. Still largely compromised of traditionalists, the awards body might not have fully understood the show, but there was a grudging recognition that it was important, maybe even that it was forecasting where television was headed. Around one week later, Sex and the City premiered on HBO. The Sopranos aired its first episode seven months later, and the transformational it’s-not-TV era was properly underway. Before that seismic shift, it was The Larry Sanders Show that demonstrated the untapped possibilities of the form. Trails require blazing.

Other posts in this series can be found at the “Golden Words” tag.