Jay Leno and David Letterman’s behind-the-scenes battle to succeed Johnny Carson as host of The Tonight Show was the biggest television story of the early 1990s, memorialized in news headlines and a bestselling book, The Late Shift by Bill Carter. Throughout that messy succession — which ended with Leno assuming NBC’s late-night perch, and Letterman moving over to CBS — the media and general public seemed to take Letterman’s side. But actor Daniel Roebuck was always in Leno’s corner… even before he was cast as the victor of The Tonight Show war in the movie version of The Late Shift, which premiered on HBO on Feb. 24, 1996.
“Bill Carter skewed his book toward Letterman, and even the movie skewed toward Letterman,” he tells Yahoo Entertainment ahead of the film’s 25th anniversary. “But I never understood Letterman. I tried to watch his show, and he'd have some science teacher from Sheboygan on. The science teacher was happy to be on TV, but Letterman would be making fun of him through the whole process. There's a cruelness to it that I just don't get. If they had wanted me to play Letterman, I don’t think I could have done it. I don’t deny that he’s a great entertainer; I just don’t like how he entertains.”
Roebuck says that he did connect with Leno in a big way, and carried that sense of identification into the audition with director Betty Thomas. “I dressed like Jay, and did the closest simulation of his voice that I could,” he remembers. “I took it very seriously. And they didn't want comedians to play those roles, because it wasn't about doing comedy — it was about doing the drama. Betty wanted to get a sense of who they were off-camera."
Part of the reason why Letterman emerged as the more sympathetic figure at the time is because of the scorched earth strategies that Leno’s manager, Helen Kushnick, employed to ensure that her client nabbed the most-wanted job in late night. As detailed in Carter’s book, and depicted in Thomas’s film version, Kushnick (played by Kathy Bates) strong-armed nervous NBC executives into promising Leno the job and even spread rumors about Carson (Rich Little), who famously hoped that Letterman (John Michael Higgins) would inherit the show. Intensely loyal to Kushnick, Leno never challenged her tactics — at least until NBC forced them to part ways — and engaged in some subterfuge himself. In one of the book’s most famous scenes, which is faithfully replicated onscreen, Leno hides in a closet and eavesdrops on a top-level meeting where network executives are deciding his future.
“I love that scene,” Roebuck says, rising to Leno’s defense. “I don’t blame Leno for what he did — I don't know any performer who wouldn't have done the same thing preserving the dream they had. I’m about to do this movie that’s the role of a lifetime, and I will tell you that if something came up that would potentially disqualify me from doing it, and if there was some kind of covert action I could take to maintain the upper hand, I would take it.”
And having been with the same managers for the majority of his career, Roebuck says that he also understands Leno’s intense commitment to Kushnick. “[Helen] was a big part of getting him all those deals, so I can see why he was loyal to her. But as recounted in the story, there’s a breaking point for everybody. I wouldn’t like it if my manger represented me in a derogatory way that’s not in my character." (Kushnick died in August 1996, six months after the film’s HBO premiere.)
Just as Roebuck is a fan of Leno’s, the former Tonight Show host — who was briefly replaced by Conan O’Brien in 2009, and permanently replaced by Jimmy Fallon in 2014 — is on the record praising the actor’s portrayal. In fact, Leno invited Roebuck and his daughter to attend one of his last Tonight Show tapings, and they caught up after the show. “Jay asked, ‘Hey Dan, how long ago was that movie?’ And I said, ‘You see my daughter? The movie is exactly her ago, because she was born the day after we finished shooting.'”
Roebuck’s acquaintance with Leno started after the film’s production as well: During shooting, he avoided contacting Leno. “I didn’t want to bother him,” he explains, adding that NBC also moved to “shut down” any association with the movie. “After it was done, I dialed his office, and said, ‘It’s Danny Roebuck calling.’ And they didn’t say ‘Who?’ They said, ‘Hold on,’ and then I heard Jay get on the line and say, ‘How’d it go?’ And as I got to know him over the course of the next so many years, he was always very gracious about it."
As Roebuck recalls, Leno’s warm reception stood in marked contrast to Letterman’s chilly treatment of Higgins. In a 1995 interview with Entertainment Weekly, the host referred to his onscreen counterpart as a “circus chimp,” and the actor — who later found fame as a scene-stealer in Christopher Guest mockumentaries and the Pitch Perfect franchise — said that he was once booked on The Late Show only to be bumped at the last moment. “John is a great actor and a great guy,” Roebuck says. “I was sad that we really only had one scene together in the movie, because I’m a big fan of his. That David Letterman felt compelled to humiliate him was disgusting. I’ve always said that I’m lucky my guy talked to me whenever I called.”
Critics generally weren’t kind to the movie either, singling out the makeup as a particular sticking point. “All the reviews attacked the makeup, but I think that’s because they were told about it,” he says, remembering the daily five-hour process of being outfitted with a foam rubber chin to play Leno. “One of the makeup artists was Monty Westmore, who had worked with Paul Newman and Dustin Hoffman. His whole family had been in the business for decades, and he would tell me about all these great stories about Joan Crawford and other legends. So it was expertly designed and applied. I thought it looked completely realistic, and it helped me greatly.”
Awards voters agreed: The Late Shift's makeup team received an Emmy nomination, and the film appeared in six additional categories, including Outstanding Made for Television Movie and supporting actor nods for Bates and Treat Williams, who plays super-agent Michael Ovitz. "It was a water cooler thing," Roebuck says of the film's reception beyond the halls of NBC and CBS, both which avoided promoting the film prior to its release. Funnily enough, some of the people who aren't flatteringly portrayed in the movie — including former NBC executive, Warren Littlefield, played by Bob Balaban — wound up being among its biggest fans. "Warren had another TV series that he wanted John and I to star in it," Roebuck says, laughing. "So he didn't hate us. Nobody hated us."
In the quarter-century since the Tonight Show battle depicted in The Late Shift, late night television has changed considerably. Both Leno and Letterman have long since retired, replaced by Jimmy Fallon and Stephen Colbert, respectively. Meanwhile, the rise of cable shows like The Daily Show and streaming services — not to mention the ease of watching morning-after highlights on YouTube — has fractured the big-tent ratings that The Tonight Show and The Late Show used to attract. At the same time, it's an environment that's allowed for an increasingly diverse group of hosts and viewpoints, from Amber Ruffin to Desus & Mario to Hasan Minhaj.
Surveying the current late night landscape, though, Roebuck says that he still misses Leno's voice — specifically his apolitical approach to comedy. "You would have never known who Jay Leno voted for," explains the actor, who characterizes himself as an "enigma" in Hollywood: a churchgoing Christian who prefers to keep politics out of his work. (In addition to his acting career, he also runs the faith-based production company, A Channel of Peace.)
"He took shots at everybody equally — same thing with Johnny Carson," Roebuck continues. "All of these guys who have late night shows now are terrific entertainers, but I don't want to know anybody's politics. I think that's what pushed people away from late night. I bet the numbers are down, because middle America doesn't watch The Tonight Show anymore. When you look at the history, Letterman had a very successful career, but Jay Leno was the Tonight Show. I feel strongly that there is a Godly plan for everybody, and it was in the plan that Jay would be the host of The Tonight Show. All the behind the scenes machinations aside, that’s just where he was going to end up.”
The Late Shift is currently streaming on HBO Max.
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