MONKEY SHINES: DAVID LETTERMAN, A PLUSH TOY AND A CABIN BOY.

From Chevy Chase, Jon Stewart and Craig Ferguson to Jimmy Fallon, Martin Short and Whoopi Goldberg, the ‘Chair Behind the Desk’ late-night hosting gig has seen a great many talented talkers ease the sting of fickle fame with a shot at chat show popularity. But one man reversed the big-to-small screen stigma, melding television immortality and movie stardom.…well, sort of. Remember David Letterman in Cabin Boy…?

Adam Resnick and Chris Elliott connected as staff writers on NBC’s Late Night with David Letterman in the late 1980s. Integral to the core creative team, the caustic Resnick and off-kilter Elliott befriended the notoriously prickly but comedy-savvy ex-weatherman, who was being groomed for the chair left empty by the great Johnny Carson. But when sly manoeuvring by rival Jay Leno infamously robbed Letterman of that spot, the Indiana native downed tools and took some months off to rework the format for a new employer, CBS.

As the high-profile ‘War for Late Night’ was unfolding, Resnick (picture, right; on The Late Show in 2014) and Elliott watched the fate of their old boss from afar, having decamped to LA. They produced two seasons of Fox’s bewildering comedy series Get A Life, described by one critic as an ‘anti-sitcom’; Resnick’s unique comic perspective attracted the likes of Charlie Kaufman and Bob Odenkirk, while Elliott upped his Hollywood profile with acting gigs in The Abyss, New York Stories and Groundhog Day.

The time was right for the writing duo to graduate to feature films. From their off-centre chemistry sprang a starring vehicle for Elliott, a weird re-imagining that combined elements of MGM’s 1937 adventure Captain’s Courageous and the Greek epic poem, The Odyssey. The pitch found favour with the Disney offshoot, Touchstone Pictures; for the mini-studio, the key factor was the chance to secure the services of the pair’s script collaborator, Tim Burton.

"Disney was sort of kissing (Burton's) ass at the time because they wanted him to make a deal there," Resnick told a packed Q&A audience in 2005. "(The film) would’ve been great, if Tim had gone through with it. But he changed his mind at the last minute." The proposed budget of $40million took a hit without Burton’s marquee name; Touchstone now wanted the same script shot for $10million. Meanwhile, the studio fostered Burton’s pet project, Ed Wood, while the director was also working on Cabin Boy. Said a circumspect Resnick in 2012, “I don’t like to disparage the people that were involved…” (Pictured, left; Burton on the set of Ed Wood).

Burton’s eleventh-hour departure did not halt production, with Resnick taking on directing duties. The shooting script followed an uppity ‘Fancy Lad’ who mistakenly boards a rustic vessel, The Filthy Whore, and finds himself at sea with a band of gruff seamen (Brion James, Brian Doyle-Murray and James Gammon), a dim-witted swabby (future Conan O’Brien offsider, Andy Richter), mythical creatures (Ann Magnuson’s randy Octo-woman; Russ Tamblyn’s half-shark/half-man) and a pretty long-distance swimmer (Melora Walters).

“My immediate reaction was, ‘I don’t know how to direct a fucking movie,’ (and) I said no,” Resnick told Splitsider in 2014. “But then all the chatter started. ‘Don’t worry, Adam, we’ll surround you with good people’ and my agents (saying) ‘Do you know how many people would kill for this chance?” In a 2014 interview with The AV Club, the director recalls, “If I were going to direct my first movie, Cabin Boy would be the last sort of thing I’d come up with. It was written for Tim’s sensibility.” The finished film would become the stuff of Hollywood nightmares; debuting January 7, 1994, on a weekend when ice storms shut down much of the US East Coast, and with a tidal wave of negative press crashing against its bow, Cabin Boy sputtered to less than $4million at the US box office. What was once touted as Tim Burton’s follow-up to Batman Begins now seemed destined for movie oblivion…

But one incredible stroke of good fortune had befallen Resnick and Elliot - the Cabin Boy shoot had taken place when David Letterman was between his talk-show commitments. It would be in those fateful few weeks that their old friend agreed to film a cameo as ‘Old Salt in Fishing Village.’ As Fancy Lad wanders a seedy coastal village, Letterman’s cigar-chomping stall owner offers the greeting, “Well, well, well, what’s on your mind, little girl?” After several awkward platitudes and off-colour observations (“You remind me of my sister, Sally. She’s a dietician.”), Letterman brings all his character actor finesse to a line reading that would seal his place in the annals of cinema history…

“Hey, would you like to buy a monkey?

“Adam and I were both really so lucky that Dave agreed to do it,” Elliott told Vulture.com. It is the only character part that Letterman has on his IMDb page, despite being listed in the end credits as ‘Earl Hofert.’ The short scene, barely a minute long, became fuel for Letterman’s caustic brand of self-effacing comedy, with references turning up many times as part of his iconic ‘Top 10 List’ (Top 10 Things Overheard at the Academy Awards - No. 9: If this goes well, I hear they'll offer Whoopi Cabin Boy 2; Top 10 Cool Things About Winning an Academy Award - No. 9: Might get offered the lead in the sequel to Cabin Boy).

When David Letterman hosted the 67^th Academy Awards in 1995, the notoriety of Cabin Boy and the profile that he had afforded his ill-fated bit part meant it was right for skewering on Hollywood’s biggest stage. Despite the professional and personal battering Resnick took following the film’s failure (he told The AV Club, “I never wanted to direct again. I didn’t have the strength to endure that level of failure and embarrassment.”), the director agreed to oversee a short that would air during the Oscar broadcast, in which some of cinema’s biggest stars reveal their Cabin Boy auditions.

The Cabin Boy creative team have both restored their tarnished reputations. Elliott would become a TV regular with recurring roles on Saturday Night Live and Everybody Loves Raymond, as well as scene-stealing turns in There’s Something About Mary, Kingpin and the soon-to-be-released The Rewrite, opposite Hugh Grant. Resnick rose to co-executive producer on the highly-acclaimed The Larry Sanders Show and penned the John Travolta/Lisa Kudrow vehicle, Lucky Numbers, and the dark Edward Norton comedy, Death to Smoochy; in 2014, he published his memoirs, Will Not Attend: Lively Stories of Detachment and Isolation.

Even their much-maligned debut feature has experienced a resurrection of sorts, with screenings and Q&A events filled to capacity with fans for whom the fresh insanity and bizarre tone of Cabin Boy represents a period of studio experimentation long since gone. “We’ve grown fonder of it over time,” says Resnick. “It’s kind of unique; it’s its own little strange thing.  And there are people out there who really like it.”

The Late Show airs its final episode on May 20; Cabin Boy is available to Australian readers via Touchstone (Aust) YouTube channel