A TV film based on the book aired on HBO in 1996 starring John Michael Higgins as Letterman, Daniel Roebuck as Leno, Kathy Bates as Leno's overbearing producer Helen Kushnick, and Bob Balaban as NBC executive Warren Littlefield.
The book features examples of:
- The Ace: Michael Ovitz. One of the best talent agents of that time, hired by Letterman to be a "hit-man" to get him out of his contractual woes one way or another.
- Played with in the TV movie where Ovitz makes his sales pitch to Letterman and Letterman's colleagues. The offer is so note-perfect and overwhelming that Letterman stumbles out of the room gasping "I feel like I was just in The Godfather!"
- Alpha Bitch: Leno's manager Helen Kushnick
- Batman Gambit: What Ovitz pulls off: Knowing that NBC has the right to match any offer for Letterman, the agent crafts out a deal with CBS that requires Letterman be on an 11:30 PM show or else receive $50 million (a serious "poison pill"). It almost gets NBC to agree to hand The Tonight Show over to Letterman... but there was still enough wriggle room to delay the turnover long enough to screw Letterman and keep Leno on The Tonight Show.
- Foregone Conclusion: Jay Leno will be host of The Tonight Show until 2009. After a brief hiatus, he will return to hostnote from 2010 until his permanent retirement in 2014. Meanwhile, David Letterman will stay with CBS until 2015, outlasting Leno.
- Old Master: Johnny Carson. Having ruled late night for decades, he had become a father figure to many a stand-up comedian — especially to both Letterman and Leno, who treated him as a mentor/father figure; it's Carson who Letterman turns to for advice before he finally decides to leave NBC. The fight over who becomes Carson's successor on The Tonight Show is what triggers the entire tragedy.
- Screw This, I'm Outta Here: Letterman decides to leave NBC for CBS after being passed up to replace Carson. Arguably, Carson himself when it became clear that he was being pushed out of The Tonight Show with no say on his replacement.
- Unwitting Instigator of Doom: Pat Sajak. His terrible late night show on CBS drove that network to pursue Leno as a replacement, triggering the entire mess.
- We Used to Be Friends: Leno helped inspire Letterman to try comedy, became one of Letterman's early supporters, and then was Letterman's most frequent guest during the early years of Late Night, which boosted Leno's profile and led to him becoming Johnny Carson's fill-in host. All that changed once Leno was selected to replace Carson instead of Letterman.
- In Real Life the rift never mended between the two. Leno tried reaching out when Letterman underwent heart surgery in 2000, but Letterman never responded. When Leno got embroiled in another Late Night war — this time with Conan O'Brian in 2010 — Letterman took potshots at both NBC and Leno for mishandling another Tonight Show transition. The two did appear together in a 2011 Super Bowl ad with Oprah Winfrey and were polite and professional towards one another, but did not renew their friendship.
- It can also be inferred that Leno's relations with Carson were irreparably damaged, since Carson both made a cameo appearance on Letterman's CBS show and sometimes contributed jokes for Letterman's monologues — honors which he never gave to Leno.
The TV movie features examples of:
- Adaptation Distillation: As formidable as Kathy Bates’ portrayal of Helen Kushnick is, some of her diatribes and confrontations from the book were either omitted (like her profanity-laced, screaming phone call with Jerry Seinfeld) or toned down. Many of the real-life players who saw the film have also said it went easy on Kushnick; she was far more vitriolic and terrifying in actuality.
- Adaptational Heroism: Leno is much more of an Anti-Villain in the movie, as it omits some of the more underhanded things he either did or signed off on.
- Bittersweet Ending: Leno gets to stay on The Tonight Show but has cut ties with friends - especially Letterman - doing so, while presiding over a show that had lost its allure during the fight to control it. Letterman moves to CBS where his late night show becomes a bigger hit than Leno's but he does so knowing he can never host the show he did want, and that he had lost friends - especially Leno - as well.
- The only ones who are happy in the end are the networks, who turn the rating boosts over the public fighting into profits.
- Bullying a Dragon:
- Letterman's mistreatment by NBC puts him in the direction of CAA agent Michael Ovitz, who was able to make the CBS deal.
- Kushnick does this to NBC when she becomes Tonight Show producer, throwing tantrums whenever things don't go her way, leading up to her pulling the plug on a live show following the 1992 Republican Convention
when Ronald Reagan's speech goes too long. It leads to a backroom war within the network against Kushnick.
- The Cameo: The movie has various Real Life participants in the fight over Tonight pop up in the background of key scenes, and various celebrities As Himself during their late-night visits to the shows.
- Sandra Bernhard appeared as herself as Letterman's guest during the opening scene. For reasons unknown even to Bernhard, she had been banned from Letterman's shows ever since, one possibility due to Letterman's hostility towards the book and movie exposing his fight to win the Tonight Show.
- When CBS executive Howard Stringer shows up to pitch his network to Letterman, he briefly mistakes someone at the bar for fellow exec Rod Perth. The guy he accidentally started talking to? The Real Life Rod Perth.
- Sandra Bernhard appeared as herself as Letterman's guest during the opening scene. For reasons unknown even to Bernhard, she had been banned from Letterman's shows ever since
- The Consigliere: Tonight Show/Late Night producer Peter Lassally for Letterman.
- Dogged Nice Guy: Jay Leno is portrayed as such, being pulled in two directions by the NBC executives and Kushnick.
- Dramatic Irony: The rush for NBC to find Carson's replacement in Jay Leno was based on The Tonight Show losing the younger audience to syndicated competitor The Arsenio Hall Show. The show wound up being cancelled in 1994 shortly after Letterman moved to CBS...taking his younger audience after the CBS affiliates that carried Arsenio displaced it to accommodate Letterman (either by pushing off Arsenio to a later timeslot or forcing the show to move to a Fox or independent station). Also, CBS initially wanted to grab Leno from NBC due to his contract as fill-in host expiring sooner than Letterman's. This resulted in NBC locking Leno to be Carson's successor... and CBS getting Letterman a few years later for their late night slot.
- Historical Villain Downgrade: While still not flattering, the film leaves out the book's descriptions of some of Helen Kushnick's even worse behavior; see Adaptation Distillation above.
- How We Got Here: The film starts with the 1993 press conference announcing Letterman's move to CBS. It later flashes back three years when CBS executives try improve their late-night programming...by turning to Leno.
- Knight in Sour Armor: Letterman. His caustic personality on stage is not an act. He's shown having a perfectionist streak and self-loathing issues. Even when he's on top of the world with his late-late night show at NBC, he's miserable.
- Loophole Abuse: Michael Ovitz was able to circumvent two blocking clauses to Letterman's contract with NBC this way:
- One clause stipulates that NBC has first negotiating position to prevent pitching Letterman to anyone but NBC. So, Ovitz decides to set up meetings so that, instead of pitching Letterman to other networks, the networks pitch themselves to Letterman, reversing the process.
- He is able to convince Bob Wright of NBC to allow Letterman to solicit other offers from other networks, both knowing that NBC still has the offer to match any deal within 30 days. (This is after Wright becomes fed up with Kushnick's stunts as Executive Producer of The Tonight Show with Jay Leno.) So, Ovitz is able to set up a deal in which CBS offers a penalty clause: Letterman gets a show that airs before midnight, or the network pays him $50 million. Since CBS is already offering him such a show, NBC will be forced to either (1)release Letterman from NBC, (2)immediately replace Leno as host of The Tonight Show, or (3)pay Letterman $50 million.
- Machiavelli Was Wrong: "Whether to be fear or loved?" when fighting over late night. Helen Kushnick is brash and demanding (and back-stabbing), yet effective in working to get Jay Leno to inherit the coveted throne of Late Night television. However she quickly makes too many enemies in the industry - especially with the network who really controls the show - and crosses the line when she starts punishing talent agencies when they won't send the hottest performing acts her way. Meanwhile, talent agent Ovitz takes the Soft Power approach when dealing with not only NBC but also all the other networks and power brokers in Hollywood, allowing him to negotiate a sweetheart deal for Letterman at CBS. By story's end, Kushnick is pretty much exiled from Hollywood and Ovitz becomes President of Disney during that studio re-emergence as a media powerhouse.
- Although, prior to Carson announcing his retirement, Helen Kushnick aggressively pushing NBC to name Leno as Carson's successor is what gets him the job in the first place, while Letterman's awkwardness in talking to executives and his refusal to get an agent to do the talking for him is part of why NBC passes him over for Leno. And Letterman's own inexperience in negotiating (which Ovitz utterly excels at) led to the one thing that could have secured him The Tonight Show — a penalty clause in his contract for if he didn't get it — being rendered useless by the "penalty" being only $1 million. Compared to the $50 million penalty clause in his CBS contract that forces NBC to let him go.
- Small Name, Big Ego: Kushnick's ego becomes so monstrous that she demands that Michael Gartner, the head of NBC News, end the network's convention coverage early when Ronald Reagan's speech goes a little long. Gartner points out to Kushnick that A.) she has no business telling Gartner how to run his news division and B.) ending the convention coverage is not his call anyway, but NBC President Robert Wright's. Kushnick then cancels the live show and sends the audience home, believing the network will blame the news division for not booting Reagan off the air. Of course, the network correctly blames her instead, making her position even more precarious.
- Pragmatic Adaptation: The film chooses to focus exclusively on the Tonight Show battle between 1991-1993, and doesn’t dramatise the tangents chronicling Leno and Letterman’s rise to power throughout the 1970s and '80s. Nor does it give as much biographical information on many of the main players, though crucial elements were highlighted in exposition (such as Leno having promised to care for the widowed Kushnick after her husband's death). The film also Bookends with Letterman’s CBS press conference, and doesn’t depict the chapters focusing on refurbishing The Ed Sullivan Theatre, his early days on the Late Show, nor the process of selecting Conan O'Brien to succeed him on NBC. This was replaced by text summaries briefly explaining some of the aftermath.
