Tom Ruprecht: Make It 'Til You Fake It

Oct 10, 2013
Originally published on October 15, 2013 12:45 pm

Want to know what J.D. Salinger was really up to during all those years as a recluse? He wrote racy letters to Ruth Bader Ginsburg, dined with Michael Jackson and cut a track with the Foo Fighters. At least, according to this week's Very Important Puzzler, Tom Ruprecht, a former Late Show With David Letterman writer and author of a totally fake oral history of Salinger's life.

Comedy writing has long been a calling for Ruprecht, who explained how he worked his way up from intern to staff writer for Late Show, and the lengths to which he has been willing to go for a comedy sketch. And why a fake oral history? Ruprecht told Ask Me Another host Ophira Eisenberg that inventing the details of Salinger's little-known life story sounded much more fun than doing actual research. Plus, he'd already written a fake oral history of former President George W. Bush. (Hear Ruprecht's story about his run-in with the White House over a Late Show joke in the web extra on this page.)

Given his penchant for the quotable, we challenged Ruprecht to a 'Who Said It?' game in which he had to distinguish quotes from Bush, Catcher In The Rye protagonist Holden Caulfield, and David Hasselhoff (from his 2007 autobiography, Don't Hassel the Hoff). By game's end, we all knew who the real Knight Rider was.

In the video below, watch Ruprecht's Late Show comedy bit that didn't go over well with the White House. (Hear the full story in the web extra.)

Copyright 2013 NPR. To see more, visit http://www.npr.org/.



Welcome back to ASK ME ANOTHER, NPR and WYNC's hour of trivia, puzzles, and word games. I'm Ophira Eisenberg and joining me is former "Late Night" writer and author Tom Ruprecht.



TOM RUPRECHT: Thank you for having me.

EISENBERG: Were you an avid reader growing up?

RUPRECHT: I was. But can I just talk about the show for a second?

EISENBERG: This show?

RUPRECHT: This show.

EISENBERG: Sure. Yeah, you can.

RUPRECHT: Because during my big shot TV career I also worked at "How I Met Your Mother."


RUPRECHT: And during that theme song segment...


RUPRECHT: ...you played a song from "How I Met Your Mother."


RUPRECHT: And I thought, oh, hey, that's cool. It's the show I worked on and I was feeling all good about myself. And then the guy buzzes in and he's like I hate myself for knowing this.


RUPRECHT: Like as if he was watching porn.

EISENBERG: I like that you got really personal about it.


EISENBERG: You're like we're going to mention this and we're going to get it settled in my interview.

RUPRECHT: But this is, you know, like, he was very proud of having watched "Save by the Bell."


RUPRECHT: Like that, he had no problem with that.


EISENBERG: Yeah. I just think it was the quantity of things he knew...


EISENBERG: ...that was starting to...

RUPRECHT: I guess.

EISENBERG: But, you know, actually, so you wrote a couple of books.


EISENBERG: And you were a writer for a television series called, well, "Late Night."

RUPRECHT: "Late Show with David" - yeah.

EISENBERG: But you did not start as a writer. Which, is that rare?

RUPRECHT: It was pretty rare.


RUPRECHT: Yeah. Yeah.

EISENBERG: Just so people know, a writer on the "Late Night," that is a - it's a big deal to get that position. You write packets. I mean, people slave away at this...

RUPRECHT: Yeah, yeah, yeah.

EISENBERG: ...for years.

RUPRECHT: A lot of people slave away. I just more got it out of attrition. I started as an intern and just bodies fell away and finally they - after enough time they - here's the thing.


RUPRECHT: OK. So, you know, I liked the Letterman show and I though, oh, well, you know, I'm curious how that works. And I heard they had internships. So I did an internship. And I, you know, liked the vibe there. And I was like, oh, wow; this would be a fun place to work. What I ultimately wanted to do was write but the writers get fired a lot. And so then I was scared.


RUPRECHT: Because I had, like, a normal job there and I was like...

EISENBERG: What was your normal job? What do you - what is a normal job, by the way?

RUPRECHT: I interned. Then I was the receptionist. Then I booked the human interest guests. And then I did research in celebrities. But then I started writing humor pieces for, like GQ and the New York Times and the folks at the show said, well, why don't you write here. And it worked out.

EISENBERG: Were you ever on camera involved in any of the sketches?

RUPRECHT: I used to be in a lot of sketches.

EISENBERG: Oh, yeah?

RUPRECHT: Yes, yes, yes.

EISENBERG: Any one come to mind that - I like failures. Any failures?


RUPRECHT: OK. Yes. Well, I have nothing but fail-right.

EISENBERG: You've had nothing but failures?


EISENBERG: Sounds like it, from your resume.



RUPRECHT: A lot of times on those shows when they do something in the audience, you know, the people in the audience are supposedly just audience members. They're not really audience members. They're plants, you know.


RUPRECHT: OK. So there was a thing where Dave was going in the audience and he was going to talk to somebody and it was me and it was a whole big prepared comedy bit that was going to come out of it. It was important that I sit in one particular seat because there was going to be some special effect or something.

And so the seat that they had mapped out turned out to be between a man and his wife. And Dave's about to come out for the monologue and the guy goes, hey, would you mind just switching seats with me? And I said, ugh. Actually, I think I've got to hang on to this one. You know?


RUPRECHT: And he's like, well, actually - but that's my wife. I want to sit next to my wife. And I said oh, oh, yeah, yeah. But if it's all the same to you I'd like to stay in this seat. And, you know, he's like, well, it's not all the same to me. That's my wife. I want to sit next to her, you know? And then he said, all right, fine. I'll give you $20.

At that point I decide I'll pretend I'm an obsessive fan, you know? Like go the Mark David Chatman route. And I was like, oh, I love Dave and I love this seat and, you know, the camera angle.


EISENBERG: The camera angle.

RUPRECHT: You know, like it was just so good. You know, his nose looks so good from this - so I was like I don't want to give up this seat. And so the lights go down. Dave comes out for the monologue and I'm nervous because I'm about to be in this bit. And Dave starts doing the monologue and the guy leans over and whispers in my ear you're an (bleep).


EISENBERG: And then you switch gears and decide to write a book.


EISENBERG: And now you're on your second book. You like fake oral histories. Do you like oral histories?

RUPRECHT: I do. I like reading oral histories. I find that they're a snap to get through. And so when I started thinking about a book I thought, oh, maybe an oral history would be fun to write. But then I realized you would have to go and do a lot of reporting and a lot of legwork and talk to people.

EISENBERG: That's sounds like...

RUPRECHT: And then I thought a fake oral history.


RUPRECHT: I don't have to leave the apartment for that.

EISENBERG: I love that you paint yourself as lazy when clearly you are the furthest thing from that. And your current book, "This Would Drive Him Crazy: A Phony Oral History of J.D. Salinger." That title describes it almost perfectly.


EISENBERG: Now, I take it to write this book, "A Phony History of J.D. Salinger," you would have to be a fan.


EISENBERG: You age? Were you one of these teenage kids...

RUPRECHT: Oh, yeah. I was - as you can probably guess I was, you know, a pathetic high school kid. You know, a loner and, you know. So, yeah.

EISENBERG: Did you carry it with you kind of thing like your Bible?

RUPRECHT: I didn't carry it with me.

EISENBERG: I know. That is, like...

RUPRECHT: I mean, I'm not a freak, you know.


RUPRECHT: But, no, no. But I liked it. Yeah, this is a guy I'm interested in and very little is known about him. I have an empty canvas to just kind of go nuts with.

EISENBERG: Well, that's so interesting you say that because that is true, but all of a sudden, your book hits.


EISENBERG: At the same time...


EISENBERG: ...in the world as they're releasing new works that they found of his. There's, like, movies out.


EISENBERG: There's some other books coming out. Did you know you were part of this trend?

RUPRECHT: No. And the only thing I can figure out, I guess that the book just was so big, you know, I mean, we're talking "Fifty Shades of Grey" numbers. I mean, it's really...

EISENBERG: Yeah, yeah, yeah.


RUPRECHT: It's really big. And so, you know, big, fat Harvey Weinstein, I think, you know, is eating his turkey leg and he sees these numbers and he's like, oh, my god; Salinger is in the Zeitgeist. You know, and so he rushes out this documentary, you know, just trying to piggyback off my success.


EISENBERG: Really. Like, he gets a bunch of his friends together. He's like who here has a J.D. Salinger - all hands go up.

RUPRECHT: Yeah, yeah, yeah.

EISENBERG: They're like we've had one for years.


RUPRECHT: Yes, that's right.

EISENBERG: Did you have to do a lot of research to write a fake oral history?



EISENBERG: Really? Very little?

RUPRECHT: See, again, there's that word fake which really helps you.

EISENBERG: Yeah, yeah, yeah. Just make it up.

RUPRECHT: Yeah. Yeah, yeah. I read one biography about him. It was this goofball biography in that - I mean, the biography was fine but the page numbers just danced around, you know? It would be like, you know, you'd be reading, like, page 250 and then the next page would be like 378. And so it would just take these wild jumps in Salinger's life because the book was, like, misprinted.

EISENBERG: It's like Salinger got to it before it...

RUPRECHT: Yeah, yeah, yeah, yeah. Monkeyed with it. Yes. Yes. Yes. So I apologize, you know, to people who read my book. There are chapters of his life that I just, you know, I couldn't deal with because I just - they weren't in the book I was reading. So.


EISENBERG: That's why you had to write a fake one.

RUPRECHT: Yeah. Franny and Zooey, I'm sorry. I just did it. I missed it. Yeah.

EISENBERG: Well, Tom, we're going to find out how much you remember from any of the stuff you read or wrote.


EISENBERG: So I'm going to ask you, are you up for an ASK ME ANOTHER challenge?



EISENBERG: Yes, you are. Tom Ruprecht, everybody.


EISENBERG: And for this game we're going to welcome back Jonathan Coulton and John Chaneski.


EISENBERG: So, Tom, we assumed - perhaps wrongly so - that you had to do some research on George W. Bush and J.D. Salinger to write these fake oral histories.


EISENBERG: And we wanted to see, you know, just how much you know.


EISENBERG: So in this game we're going to read you some quotes.

RUPRECHT: Oh, man.

EISENBERG: And you have to identify whether it's a quote from President Bush...


EISENBERG: ...or a line from "Catcher in the Rye" which is narrated by its protagonist Holden Caulfield.


EISENBERG: And because in comedy everything is in threes, we've also thrown in some quotes from David Hasselhoff's 2007 bestselling autobiography "Don't Hassel the Hoff."



EISENBERG: So if you get enough right, Mary Elizabeth Hardin from Madison, Wisconsin is going to win a special ASK ME ANOTHER prize.


EISENBERG: OK? So the pressure is on.


EISENBERG: So you understand the premise? It's George W. Bush.


EISENBERG: Holden Caulfield.


EISENBERG: Or David Hasselhoff.

RUPRECHT: The big three.

EISENBERG: The big three.

RUPRECHT: The three Musketeers.

EISENBERG: They're always together.


EISENBERG: Here we go. Women kill me. They really do. I don't mean I'm oversexed or anything like that, although I am quite sexy.

RUPRECHT: That would be Holden Caulfield.

EISENBERG: That is correct. Yes.


EISENBERG: Could be the Hoff.


EISENBERG: Has a little Hoff about it.

RUPRECHT: He is sexy. Yeah.

EISENBERG: He is sexy.


JONATHAN COULTON: All three of them think they're sexy so it's fun.


COULTON: Could be any one of them. I had no desire to go to Wall Street. I used to tell friends that Wall Street is the kind of place where they will buy you and sell you but they don't really give a hoot about you so long as they can make money off you.

RUPRECHT: I'm going to say Bush.

COULTON: That's right. It's Bush.


RUPRECHT: The guy who then went to Harvard to get his MBA. You know, like he's all above Wall Street.


COULTON: Right. Exactly. Yeah.

EISENBERG: Yeah. When was this taken from, this quote? Was that when he was a child? We will never know.


EISENBERG: I borrowed dad's car, carelessly charged in reverse and tore the door off. I poured vodka in the fishbowl and killed my little sister Doro's goldfish. But despite it all, my parents still loved me.

RUPRECHT: Mm-hmm. Yeah, that would be our former president, George W. Bush. Yeah.


EISENBERG: It's a little frightening even now, isn't it? Yeah.


COULTON: Just a guy you'd want to hang out and have a beer with. That's the thing.


COULTON: Back at the hotel, a group of air stewardesses had arrived in the lobby and this led to an all-night party in my room with what seemed like the entire staff of the airline. I don't remember if anything was consummated. There was a lot of drinking and hugging and laughing and no one got any sleep.

EISENBERG: OK. These are not supposed to be your own quotes, Jonathan Coulton.


COULTON: Oh, that's - I'm reading that.

EISENBERG: OK. All right.

RUPRECHT: I've got to go with the Hoff there.

COULTON: It's the Hoff, all right.



EISENBERG: I don't much like to see old guys in their pajamas and bathrobes anyway. Their bumpy old chests are always showing. And their legs - old guys' legs at beaches and places always look so white and unhairy.

RUPRECHT: Now, I mean, that could be Bush talking about Cheney.


RUPRECHT: But I think that's Holden Caulfield.

EISENBERG: That's is correct.


COULTON: This one is deceptively simple.




COULTON: I salute you, sir. That was a fine, fine joke. Well done. I went outside and screamed I am the Knight Rider! I am the Knight Rider! Get it together, man. You're here for a reason. Come on!


RUPRECHT: I am going to say David Hasselhoff.

COULTON: No, I'm sorry. It was George Bush. It was George Bush.

EISENBERG: It was George Bush.

COULTON: No, it was Hasselhoff.

EISENBERG: That's right.


EISENBERG: Chaneski, how did our VIP Tom Ruprecht do in that quiz?

JOHN CHANESKI: Ruprecht got a perfect score. He got them all right. Way to go, Tom.


EISENBERG: Congratulations. You and Mary Elizabeth Hardin from Madison, Wisconsin will receive an official ASK ME ANOTHER Rubik's Cube. I know. Limited edition. One more round of applause for our VIP, Tom Ruprecht.



COULTON: (singing) I'm your only friend. I'm not your only friend, but I am a little glowing friend. But really, I'm not actually your friend. But I am - I have a secret to tell from my electrical well. It's a simple message and I'm leaving out the whistles and bells. So you must listen to me. Filibuster vigilantly. My name is Blue canary, one note, spelled L-I-T-E. My story is infinite.

(singing) Like the Longines Symphonette it doesn't rest. Blue canary and the Alabama light switch. Who watches over you? Make a little birdhouse in your soul. Not to put too fine a point on it, say I'm the only bee in your bonnet. Make a little birdhouse in your soul.


EISENBERG: Jonathan Coulton. Transcript provided by NPR, Copyright NPR.