Remembering ‘The Late Shift,’ The 1996 Made-For-TV Movie That Immortalized The Late Night Wars

All this week,
Uproxx‘s Late Night Week will take a look at late-night past, present, and future, from talk shows to late-night comedy, and beyond. Here’s a look back at a memorable, oft-aired HBO movie that retold the battle between Jay Leno and David Letterman using a compelling mix of drama and cheese.

When I was growing up in the early ’90s, I was obsessed with a lot of things that now seem a little silly: grunge, NFL passing statistics, Elle MacPherson, Total Recall. But by far the silliest, and hardest to fathom, was my intense interest in the late-night wars waged by David Letterman and Jay Leno over The Tonight Show.

How this inside-baseball story spilled over into the tabloids and Bill Carter’s 1994 bestseller The Late Shiftand even spawned a sequel decades later starring Conan O’Brien — stills boggles the mind. Looking back, what should’ve been obvious all along now can’t be denied: This was an argument by millionaire entertainers over a time slot. A time slot! Remember time slots? That was when you had to tune in to a specific over-the-air channel at a specific time of the day in order to watch a show, or else you wouldn’t be able to see it, like, ever again. Can you imagine the indignity?

Nevertheless, at the time I found the palace intrigue so fascinating that I didn’t question why, in 1996, The Late Shift was turned into a TV movie that subsequently aired on HBO and basic cable approximately one billion times for the next 20 years. Instead, I proceeded to watch The Late Shift one billion times.

On paper, The Late Shift doesn’t seem remotely cinematic, even on a small screen — how do you visualize a story in which white men in suits talk about scheduling for 90 minutes? This is an inherently unsexy story, in which the hottest cameo comes courtesy of Ken Kragen, personal manager to outlaw country Muppet Travis Tritt, a marginally famous insider who was among the Hollywood elite spurned by Leno’s infamous executive producer, Helen Kushnick, over (you guessed it!) the scheduling of talk show guests. In the ’90s, when you messed with someone’s schedule, that was grounds for war! In those terms, The Late Shift is like the Saving Private Ryan of scheduling.

Translating the non-visual elements of The Late Shift to film was a challenge. But the biggest obstacle no doubt concerned the depiction of Letterman and Leno, two famous people at the height of their notoriety. Casting is a problematic issue for a normal biopic, in which the subject is typically deceased or much older than the time period being dramatized. But the casting problem was compounded for The Late Shift, a period piece set only a few years in the past, as viewers were used to seeing the actual David Letterman and the actual Jay Leno on television for up to five hours per week.

How do you portray these guys convincingly? You either have to find someone who can do a straight-up impersonation, or (preferably) a more subtle performer who can capture the real person’s essence. For The Late Shift, director Betty Thomas seems to aspire to the latter but more often than not veers toward the former, most egregiously by casting famous funnyman Rich Little as Johnny Carson. This is like casting Dana “Not Gon’ Do It” Carvey for a George H.W. Bush biopic (and just a notch above casting Dana “Weird, Wild Stuff” Carvey for a Johnny Carson movie).

As Letterman, John Michael Higgins is more nuanced, though just barely. Higgins became semi-famous after The Late Shift as a dependable comic character actor in the Pitch Perfect films and Christopher Guest’s mockumentaries, with a specialty for playing broadly drawn jerks and making them seem human. But in The Late Shift, Higgins works in reverse, turning a flesh-and-blood human into a one-dimensional creep. That’s not necessarily a criticism of Higgins — the film requires him to play Letterman as an irascible, perpetually miserable, cigar-chomping crank. (Letterman, predictably, hated the movie.)

If Higgins’ Letterman feels a little cartoonish, Daniel Roebuck’s Jay Leno is full-on Looney Tunes. With his squeaky voice, all-denim wardrobe, and well-known penchant for classic cars, Leno in real-life already seems like a caricature. So, it was probably impossible to play Leno and not have it instantly devolve into parody. There’s only so much you can do with a Subway sandwich affixed to your jaw.

Re-watching The Late Shift recently, I realized that the narrative of this film played a primary role in shaping the public’s understanding of the Leno vs. Letterman rivalry. Both Carter’s book and the film turned the fight over The Tonight Show into an archetypal “tortured genius” tale, with Letterman as the visionary and Leno as the non-genius who thwarts the hero. I was amenable to that narrative as a kid because I worshipped Letterman — his acerbic view of celebrity as host of Late Night has since become ingrained in internet culture, but in an era of TGIF sitcoms and Milli Vanilli videos, Letterman was a rare oasis of irreverent “this is all bullsh*t” sanity.

For the purpose of this narrative, The Late Shift had to play up Letterman’s self-flagellating perfectionism, as well as Leno’s Machiavellian fumbling. But while the film’s sympathies lie with Letterman, Leno emerges as the more interesting character, similar to how F. Murray Abraham’s Salieri overshadows Tom Hulce’s Mozart in Amadeus.

In 2010, when anti-Leno sentiment reached a new high in the wake of his Tonight Show feud with Conan O’Brien, Patton Oswalt compared Leno to Richard Nixon, the Diet Coke version of likening someone to Hitler. I wonder if that impression was subliminally implanted in Oswalt’s brain by The Late Shift, which connects Leno (an awkward, hard-working striver with a fat head) to Nixon (an awkward, hard-working striver with a fat head) with subtle (and not-so-subtle) visual cues throughout the film. Here’s one that’s not-so-subtle:

The central conflict in The Late Shift isn’t really Leno vs. Letterman, but rather Leno vs. Kushnick, his long-time manager. In the film, the Leno/Kushnick relationship is depicted as a classic example of co-dependent dysfunction, with Kushnick acting as the evil henchman that Leno needed to do his dirty work, and Leno as “a good son” committed to protecting his mother figure. Kushnick is the one that orchestrates Carson’s departure (by planting a story in the media about NBC pushing him out), and she’s the one who strongarms NBC into backing Leno over Letterman. Leno feels indebted to Kushnick, but her erratic behavior eventually makes her a liability. Leno must find the strength to overcome his loyalty to Kushnick and fire her, in order to save his own job.

Beyond the leads, there are three great performances in The Late Shift, starting with Bates as Kushnick. Five years removed from winning the Oscar for Misery, Bates’ ability to play an unhinged middle-aged woman who makes the men in her orbit supremely uncomfortably had only improved. Bates approaches every scene in The Late Shift like Alec Baldwin in Glengarry Glen Ross, relishing the unrelenting obscenity and bullying swagger of her outsized character. Only Bates, unlike Baldwin, isn’t just in one scene, she in almost every scene. For Kushnick in The Late Shift, “You f*ck me, I f*ck you back good” isn’t a threat, it’s a mission statement. (Kushnick, predictably, hated the movie.)

The second great performance is by Bob Balaban as weaselly NBC president Warren Littlefield. Balaban, like Higgins, is part of Christopher Guest’s repertory company, though he’s been a comic master of alpha-male passive-aggressiveness in countless other films and TV shows for decades. Perhaps Balaban’s greatest achievement as an actor was turning Littlefield into a franchise character — first on Seinfeld, as the Littlefield stand-in Russell Dalrymple, and then in The Late Shift as the film’s perpetually put-upon signifier of corporate stoogery. A potentially minor scene in which Kushnick and Littlefield argue over placement of a pro-Leno newspaper ad — again, the stakes could not be lower in The Late Shift — is turned by Balaban into a minor masterpiece of impotent comic rage.

The most celebrated performance in The Late Shift, rightly, is Treat Williams as super agent Michael Ovitz. Whatever Justin Timberlake brings to The Social Network, Treat Williams supplies to The Late Shift — he makes a business pitch sound as stirring as a pop song. Ovitz doesn’t merely spout platitudes about how it’s cool to be a billionaire, however. His vision is more holistic. “We have a career plan for David, and it includes securing everything for Dave that he wants,” he says with a born seducer’s directness. (What does Dave want? Favorable scheduling, of course!) If Ovitz was five percent less confident, you’d want to punch him. Instead, you want to hire him. Who among us doesn’t feel disturbingly unrewarded? Who doesn’t also seek to reverse the process?

The genius of The Late Shift is that its weaknesses are turned into strengths. What could’ve been a cheesy TV movie — what often is a cheesy TV movie — becomes something more. A little cheese is an essential ingredient for what The Late Shift sets out to do, which is to transform a story about relatively inconsequential show-business double-dealings into something grander, even operatic. Exaggeration is exactly what this story needed. It’s why The Late Shift lives on as the ultimate HBONow movie.