The Man Who Would Be Kingsley (Gary Shandling, Jeb Bush, Frank Sinatra, Jr. and Hank Kingsley)

You could picture Gary Shandling viewing this comically grotesque presidential campaign season and wincing in recognition. And not necessarily because Senator Bernie Sanders has an older brother named Larry. Early on, this excremental spectacle was reminiscent of Caddyshack, with Donald Trump as Rodney Dangerfield and every other politician, Republican and Democrat, as the country club snobs who despise him. In particular, Jeb Bush made a memorable foil to Trump, like how Ted Knight was to Rodney.

But the more appropriate comedy film/show antecedent is Shandling’s The Larry Sanders Show from the ‘90s, especially how this wretched election resembles a never-ending version of the roast episode. Larry’s sidekick, the unbearably phony suck-up Hank Kingsley (Jeffrey Tambor at his best, which is saying something) is so concerned about the roast for Sanders that he works on jokes with the head writer of the show. Like many current politicians, Kingsley had the great misfortune of being an unlikable person whose main purpose in life was to be liked. Because of this, Kingsley would become a rich target during the roast, which featured everyone from Carl Reiner to a pre-Daily Show Jon Stewart, and his pathetic comebacks to Stewart reeked of anxiety, jealousy, and unwarranted entitlement. Much like how Jeb would react to Trump tearing into him during the roasts … I mean, debates.

In fact, watching Jeb this past year was like seeing Hank Kingsley run for president. Imagine that, the man who would be King instead turned out to be Kingsley. It was a strange, unexpected development, considering there are those who think he was an exceptional Governor of Florida. Perhaps he was. However, you wouldn’t know it by his campaign, which was marked by a series of awkward moments that were Kingsleyesque. Even the goofy explanation point (Jeb!) was pure Hank.

When Barbara Bush went campaigning for her son, Trump mocked Jeb, saying, “He desperately needed mommy to help him.” It was hard not to feel bad for Jeb, but more so for America having to witness a presidential contender get such a savage neutering from another presidential contender. Just when you thought it couldn’t get worse, Jeb whined in response, “He made fun of my mother.” Actually, Trump made fun of him for being weak and Jeb’s feeble Hank reply only proved him right.

Then there was the time he pitifully implored an apathetic New Hampshire crowd to “Please clap.” It was the kind of cringeworthy plea for attention that made Hank Kingsley such a perfect vessel for Shandling’s observations on how desperate some people are for the approval of others. The most noxious example of this was last October, when Jeb tried to impress the NRA by dismissing the mass shooting in Oregon that had just taken place with “stuff happens.” Nine innocent people were killed and another nine wounded.

By the time he mercifully called it quits, the campaign flushed $130 million down the toilet, made Al Gore’s inept, lackluster 2000 run seem like a paragon of competence and inspiration, and (perhaps temporarily) put a humiliating end to one of the most powerful political dynasties in American history. If that’s not bad enough, there’s also the colossal embarrassment of finishing lower in numerous primaries than Dr. Ben Carson, a man who once boasted of his attempt to hit his own mother with a hammer, have that refuted by the press, and then double-down, insist it was true, while accusing the press of “smearing” him. Even Hank might’ve shaken his head in disbelief on how poor Jeb could’ve fallen so low.

This past year showed that not even someone as privileged as Jeb Bush is immune to the absurdities and cruelties of life, self-imposed or otherwise. On The Larry Sanders Show, Shandling explored and reacted to that theme, sometimes with merely a pained smile or a grimace. And the deadpan non-reactions of many Jeb crowds brought to mind The Larry Sanders Show’s pioneering use of uncomfortable silence as a punch line. You would later see it utilized on Curb Your Enthusiasm, Arrested Development, Veep, Modern Family, The Office and seemingly every commercial now airing. As a testament to his genius, the show within The Larry Sanders Show was more compelling than most of the modern late night talk programs. Shandling did a stellar job guest hosting The Tonight Show, and his intelligence, self-deprecating charisma, timing and curiosity shone through in a fictional context as well.

He also broke new ground with It’s Garry Shandling’s Show, from the ‘80s. It came off as a fusion of Mister Rogers’ Neighborhood and Late Night with David Letterman, deconstructing the sitcom format in the same irreverent, accessibly avant-garde way Letterman did with talk shows. It’s Garry Shandling’s Show could find humor in the most unlikely situations, like with Gilda Radner. In 1988, a year before she died of cancer, Radner made an appearance as herself, acknowledging her disease and mugging for the studio audience, shaking her clasped hands in a victorious, self-congratulatory manner, as if to say, “Look at me, I’m still here! Aren’t I great?!”

Any kid in the ‘80s who loved comedy connected to that unforgettable scene in Freaks and Geeks when Bill came home from school and watched a young Shandling do stand-up, set to The Who’s “I’m One.” He laughs hysterically, possibly seeing an older, more confident reflection of himself, and feels less alone. It pulls off the trick of the viewer relating to someone on TV at the same moment they’re relating to someone on TV. When Shandling suddenly passed away last month, it was one of the first things that came to mind.

Frank Sinatra, Jr. preceded Shandling in death by a week. Like Jeb Bush, he grew up with every possible advantage, and yet couldn’t escape the brutal indignities of existence, even after his own existence ended. An NBC news affiliate in Indiana announced his passing, accompanied by an image of Joe Piscopo as his father, back when he parodied him in the ‘80s on SNL. No one could imagine how hard it must’ve been living in the immense shadow of one of the 20th century’s greatest artists, plus having the same name as him. Mistakenly using a photo of his father would’ve been enough of an insult. But presenting a picture of a guy who pretended to be his father three decades ago? In life he was eclipsed by his father. And now in death by his father’s greatest impersonator.

It was the kind of cruel absurdity that, if he were watching, you could picture Shandling wincing in sympathy.

Matt Leinwohl

Leave a Reply

Your email address will not be published. Required fields are marked *