How David Letterman’s Intern Turned Superstar Really Felt About Working On The Late Show


  • Jimmi Simpson, who played Lyle the Intern on David Letterman’s show, had a meaningful experience.
  • He liked working with Letterman.
  • Simpson had no real off-camera relationship with Letterman.

After many years of success, David Letterman has gone down in history as one of the best talk show hosts. As a result, Letterman accumulated an impressive fortune which has allowed him to lead an incredible lifestyle.

Despite all of Letterman’s success, the fact is he could be prickly, which is why several guests walked out during interviews. Given Letterman’s complicated reputation, it is fascinating to see what a celebrity who worked for the talk show host said about his experience.

What It’s Always Sunny In Philadelphia’s Jimmi Simpson Thought About Working For David Letterman

In 2022, David Letterman’s YouTube channel uploaded a video dedicated to Lyle the Intern. A character brought to life by It’s Always Sunny in Philadelphia’s Jimmi Simpson, Lyle the Intern appeared on Letterman’s show during the 2000s. As a part of that video, Simpson explained how he feels about having played Lyle the Intern.

Jimmi Simpson smiling
Via: Instar

At around the halfway point in the video, Simpson spoke about his character’s relationship with Paul Shaffer. Even though Letterman was always the star of his talk show, it was talking about Shaffer that inspired Simpson to really reflect.

As Simpson explained, getting to work with Letterman and Shaffer was an extremely meaningful experience for him.

“What I started, like, deciding to have a relationship with Paul, Like I was Paul’s kind of fan. That made me feel so blessed because I’ve been such fans of both of these guys. To act in, as part of a bit, my deep love of Paul, um almost creepy, almost like a sensual appreciation of Paul…”


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Earlier in the video, Simpson spoke about what it was like to work with Letterman. According to Simpson, Letterman did whatever he wanted so he couldn’t just rely on the dialogue that was written for him.

What talk shows is David Letterman best known for according to Britannica?

Talk Show:

Premiered In:

Ended In:

Late Night with David Letterman



Late Show with David Letterman



My Next Guest Needs No Introduction with David Letterman



“The scripts were tight AF, but there was, not just room for improv, there was demand for improv. Mostly because Dave seems to say whatever the hell he wants, and you have to keep up with it. So, um, when he gets a little idea in his head and he drops it on you. Un all of a sudden the cue card are in the ether, and it’s all, it’s the wild west.”

David Letterman Interview
Via: Deposit/Commons Licences 

While Simpson made it clear that it was thrilling to work with Letterman, that doesn’t mean the two performers became close. Instead, Simpson explained during the video that he only really had one off-camera interaction with Letterman.

“Did Dave ever speak to me off-camera? Um, yes. We had one exchange… There’s a moment before filming and we’re sitting next to each other and it was quiet, and so I said, ‘Hey Dave.’ And he said, ‘No.’ and then he walked away so that was our exchange.”


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As hilarious as that story is, Simpson then quickly went on to reveal he’d just completely made it up. However, it is still worth including the made-up story here as it appears to be emblematic of the relationship Simpson and Letterman really had. After all, Simpson then went on to get serious as he explained he never had a real relationship with Letterman at all.

What are Jimmi Simpson’s Most Notable TV Roles?

  • It’s Always Sunny in Philadelphia
  • House of Cards
  • Late Show with David Letterman
  • The Newsroom
  • Psych
  • Westworld
  • Black Mirror

“We had no exchanges. I’ve never spoken to Dave Letterman outside of being Lyle the intern.”

David Letterman waving
via CBS

After revealing that he had no relationship with Letterman, Simpson went on to tell an anecdote about that. According to Simpson’s story, Letterman kept a lot of people he interacted with on his show at arm’s length. On top of that, Simpson’s story revealed that Lyle the Intern made an impression on a major celebrity.

“I think that’s just how it is actually. I was on a plane going to shoot something and, um, I saw Billy Crystal there. And it’s Billy Crystal, my goodness, and so I walked over there and said, ‘Excuse me Mr. Crystal. I just wanted to say..’ And he, ‘Lyle, Lyle the intern.’ I said, ‘Yes sir. Yes sir.'”

Simpson continued, “And then he’s like, ‘You ever, you ever meet Dave?’ And I was like, no, uh no I haven’t but, you know, it’s, that’s just, I think, that’s the way it is and I’m just happy to be a part of it’ (Billy Crystal responded) ‘I’ve known him for twenty years, I’ve never met him.’ So, I don’t know if he was kidding, but I think that’s just kind of how he is.”

How Jimmi Simpson Was Hired To Be Lyle The Intern On Late Show With David Letterman

During Jimmi Simpson’s career, he has starred in a slew of movies and TV shows. Simpson has also been so celebrated as an actor that he has been nominated for an Emmy and a British Academy Television Award. Despite all that, Simpson is still so associated with Lyle the Intern that The AV Club asked him about the character in 2016.


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While talking to The AV Club, Simpson explained how he was hired to portray Lyle the Intern. As Simpson explained, he was working on a Broadway play near the location where Letterman’s talk show was filmed. Two of Letterman’s writers who conceived of Lyle the Intern saw an image of Simpson on the poster for the play and thought he was perfect for the role.

“I had no business being there, but I was there and my picture was on posters. And the two writers at the time, the Stangel brothers, were walking by my theater and they had just conceived of the idea of having an a****le come on stage as an intern for Dave. And they saw my face and they said, “That looks like our guy.”

Jimmi Simpson looking disheveled
Via: Deposit Photos

Simpson then went on to describe how he had a whirlwind experience before portraying Lyle the Intern for the first time.

“They called my agent and said, “Hey, David Letterman wants you to do a thing before your show. Like, do a thing.” I’m like, ‘Yeah, I’ll do a thing.’ And so I went in, and I talked to the brothers and they showed me what they had written and then I read it through with them. And then after the top 20, they just pushed me on stage and said, ‘Just go sit down and do the lines.’”

Simpson continued, “And there were cue cards, I probably said half of them. And Dave and I gave each other some s**t. I was so unaware of what was happening. I’m used to live theater so it’s—it wasn’t like a big deal, but it was just like—Letterman was talking to me. And I was there with him. And it just worked.”

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