The End of Bored to Death and How to Make It in America: Bidding Farewell to HBO’s Brooklyn Duology

Bryan Greenberg and Victor Rasuk in HBO's How to Make It in America.

A new year is upon us and HBO viewers certainly have a lot to look forward to in 2012: the official launch of Luck (starring Dustin Hoffman and Nick Nolte) at the end of January; the US premiere of the new Ricky Gervais BBC/HBO comedy, Life’s Too Short, in February; and a brand new season of Games of Thrones in April. But it turns out that HBO’s full schedule comes at the cost of two of my favourite, if less often celebrated, comedies: at the end of December HBO announced that Bored to Death and How to Make It in America would not be returning in 2012. Despite airing on HBO, both series have lived pretty much under the radar since their respective premieres, and their sleeper status unfortunately did not save them from the chopping block.

Ever since the shows first premiered a couple of years ago – Bored to Death in September 2009, with How to Make It in America taking over its timeslot in February of the next year – I’ve always thought of them as a pair: both shows were Brooklyn-centred comedies, and both, more significantly, came with Jewish male actors playing explicitly Jewish main characters. Even in this post-Seinfeld century, it is still rare to find shows with explicitly Jewish lead characters, and here suddenly were two! (No, Howard Wolowitz doesn’t count!) To be fair, Jason Schwartzman’s character on Bored to Death is perhaps a more familiar New York Jewish type (in the Woody Allen vein), but Bryan Greenberg’s Ben Epstein on How to Make It in America just may have been the single hippest Jewish male character in TV history. Despite its cancellation, I hope that this promises more cool, attractive and relatively non-neurotic Jewish characters in years to come.

HBO doesn’t like to cancel shows – to its credit this is the same network that gave David Simon five full seasons of The Wire and has supported Simon’s Treme into a confirmed third, and likely fourth and final season, despite their respective struggles in the ratings – but when HBO does cancel shows, it is often heartbreaking. (Part of me will never quite forgive HBO for cutting Deadwood short after only three seasons.) With only three seasons of Bored to Death and two seasons of How to Make It in America, HBO has cut down two great shows, both still in their prime.

Jason Schwartzman, Ted Danson and Zach Galifianakis in Bored to Death.

Based on a short story by Jonathan Ames (also on board as executive producer and writer), Bored to Death offers a playful mix of urbane comedy and noir fiction. Jason Schwartzman (Rushmore) stars as a fictionalized Jonathan Ames – a Brooklyn-based novelist who, suffering from writer’s block and despair following the publication of his first novel, decides to become an unlicensed private investigator. Armed only with a Raymond Chandler novel in the pocket of his long trench coat and brief ad on Craigslist, Jonathan – often with his friends Ray (comedian Zach Galifianakis, The Hangover) and George (Ted Danson) – stumbles clumsily into the life of a not-so-hardened detective.

Beginning with his recurring appearances on Curb Your Enthusiasm and his stunning turn as the evil Arthur Frobisher in the first season of FX’s Damages, Ted Danson’s recent cable work has been nothing short of a revelation. (Danson returned to network TV this past September, replacing Laurence Fishburne as a regular on CBS’s long-running crime drama CSI.) But you haven’t seen Danson until you’ve seen his portrayal of George Christopher on Bored to Death.

As an aging womanizer and the magazine publisher, Danson plays George with an unashamed glee that rivals the more famously shameless antics of his co-star, Galifianakis. Though the only things their two characters – Ray (Galifianakis), the struggling comic book artist, and George, the mid-60s publisher of an established New York magazine – share are a deep affection for Jonathan and a love for smoking pot. Bored to Death’s most brilliant and hilarious moments came from these two very different actors playing off one another.

With a distinctive recipe of literary pretension, marijuana haze, and raw physical sexuality Bored to Death is alternately (and sometimes simultaneously) cerebral and carnal. Paying tribute to the literary origins of the story, characters are allowed to unselfconsciously and poetically speak their minds, making for a perverse kind of omniscient narration sans narrator. The result is a surreally sincere and often profane access to the characters’ inner lives, and is the source of the show’s most tender and funny moments. (For example, George’s unvarnished and sexually explicit confessions of continuing love for his ex-wife from the first season.)

The world of Bored to Death is a slightly pitched version of reality: hard-boiled New York City cops harbour SM fetishes, armed thugs quote Oscar Wilde, and writers for The New Yorker settle their differences in the boxing ring. As one might expect from an adaptation of a short story originally published by McSweeney’s, the show can sometimes err towards the precious (especially with Jonathan’s standalone storylines), but there are instances of sublime hilarity in each and every episode.

Victor Rasuk and Luis Guzmán in How to Make It in America.

Bored to Death will be missed, but the loss of How to Make It in America – well-cast, well-written, and full of heart and smarts – is the more painful tragedy of the two. How to Make It in America tells the story of two longtime friends, Ben Epstein (Bryan Greenberg, One Tree Hill) and Cam Calderon (Victor Rasuk, ER), who launch a fashion line of vintage T-shirts and jeans to try to break free of their entropically degenerating lives. The main story arc of the series – the struggles of Ben and Cam to make it in the fickle world of New York fashion – is genuinely compelling, and as are the many parallel stories of success and failure that surround them.

When it premiered in 2010, How to Make it in America seemed destined to become a kind of East Coast incarnation of Entourage – a regrettable comparison as the new show launched at a time when Entourage was firmly down its road to late life decline. Still, the association was not unfair on its face: How to Make it America was produced by the team of Steven Levinson and Mark Wahlberg, who created HBO’s Entourage (though they were also the force behind In Treatment and later, Boardwalk Empire). With its 20-something cast and pointedly drawn stories of male friendship, How to Make It in America’s delightful first episodes were indeed reminiscent of the very best of early Entourage – but that was only where it began. The first episodes followed the well-trodden formula of Entourage’s early seasons: things go awry but friends win out and nothing turns out as badly as we and they fear it might. But unlike the boys of Entourage, the characters of How to Make It in America are rarely their own worst enemies. These are people viewers can root for: Ben and Cam’s earnest fashion ambitions, Ben’s ex-girlfriend Rachel (Lake Bell, Boston Legal) and her aimless wanderings in search of herself, Cam’s cousin Rene (Luis Guzmán, John from Cincinnati), an ex-con who decides to start hocking an energy drink in an attempt to become a “legitimate businessman” (a phrase I’ll never be able to hear again without hearing Guzmán’s voice in my head). The recent season in particular had Rachel’s character emerge from the background to become one of the most impressively flawed and neurotic female characters in current television comedy. This is especially notable in a television season that has publicly re-embraced female goofiness – with Zoe Deschanel in New Girl and Whitney Cummings in Whitney. The series found stronger and stronger voices for its ensemble cast with every passing episode, and by its second (and regrettably last) season, had – in my opinion – surpassed its West Coast sibling.

And the very pragmatic differences between Entourage and How to Make it in America are precisely what makes How to Make it in America such a special series, and what made it significantly less of a bubblegum show. These characters’ lives are not shiny – there are no fancy cars, movie premieres, or one-night stands with young pop stars to hit the audience over the head with their successes, or drunken fits in strip-clubs to mark their failures. The drama and the comedy come from the pressures and realities of life’s real struggles, what Sean Rasmussen recently perceptively identified as “small stakes storytelling.” How to Make it in America is a unique pleasure, and the genuine trust and affection between the main characters gives the show a humanity that belies its hipster façade.

As we all look forward to a new year of television viewing, we should not be afraid to look back at Bored to Death and How to Make It in America (both are available on DVD and On Demand): with no new episodes forthcoming, I’ll be re-watching episodes of both shows for years to come.

– Mark Clamen is a writer, critic, film programmer and lifelong television enthusiast. He lives in Toronto, where he often lectures on television, film, and popular culture.