Jeremy Weiner: The reason Dave used Rupert and Biff was because they were genuine. They weren’t trying to act or be on the show. The fact that they weren’t actors and didn’t want to be on the show is what made them special.

Rupert Jee runs the Hello Deli in New York City. As Dave was fond of saying, “There are hundreds and hundreds of delis in New York City and the Hello Deli is . . . one of them.” With all due respect to Dave’s joke, there was one thing that distinguished Hello Deli from the hundreds and hundreds of other delis: it was only a few steps away from Dave’s studio. Within a moment, a cameraman could walk out the “Bill Murray Doors” in the Ed Sullivan Theater at 1697 Broadway, take a few steps down 53rd Street, and be in the deli. Inside this very small space, Dave would play games with contestants plucked from the street or just pop in to talk with Rupert. As time went on Rupert Jee become one of the regulars and part of the Late Show family.

Bill Scheft: We are not even on CBS yet. We were in the conference room and [writer] Spike Feresten said, “You know that guy who runs the deli, Rupert? Let’s make him a star.” I will never forget that.

Rupert Jee: Really? I never knew that.

Bill Scheft: Rupert could have come and gone. Dave is notorious for getting tired of premises. So the fact that Rupert was on virtually every week for the history of the show says a lot about Rupert and that he did not change. 

Rupert Jee: That is the irony of this whole thing. During the first two weeks, I heard they were doing these segments visiting the neighborhood. When I was in college, I deliberately avoided speech class because I didn’t want to be in front of an audience. I told the head writer that they didn’t have to come in. I was thrilled they were in the neighborhood, but they could skip me because I didn’t want to be on television. But they gave me a surprise visit early on, and my second career started. 

Rupert Jee working in the Hello Deli in 2018. Photo by Scott Ryan

Lee Ellenberg: The writers loved Rupert. There is not an ounce of irony or sarcasm from Rupert. It comes from a sweet place in him. No matter what outrageous thing Dave would say to him, he would just say, “Oh, really?” I would love Rupert segments because I would look over at Steve Young and he would be laughing so hard he would be wheezing. Maybe, as comedy writers, it was those things that made us laugh instead of jokes. 

Bill Scheft: I’ll never forget when Dave was heckling him to get a Slurpee machine. Rupert breaks down and gets the machine and Dave says, “What do you say, for today Slurpees ten cents apiece?” And Rupert said, “You mean just till the end of the taping?” Rupert was dead serious. “I am not losing money.” That was what was so appealing about him. He was money in the bank. It was an inconvenience for him to be on television and to keep his store open past 5:30.

Lee Ellenberg: We loved writing for him because we loved his flat, unironic, genuine delivery. There is a sweetness that we found hilarious, and not in a mean-spirited way—to be able to put jokes in his mouth with that delivery. Jokes are best when they are told by someone who pretends they are not funny. That was what we were told from Dave. Everything is flat, we are not in on the joke. When I would shoot a piece with Jerry Foley, I would always say, “Let’s shoot one more just a little flatter.” To me Rupert has that absolute pinnacle of earnest flatness, which sounds like an old-time banjo duo.

Barbara Gaines: Rupert just answered questions and did what we asked. He was the perfect straight man. 

Lee Ellenberg: That is why in the “Fun With Rupert” segments the joke is really on Rupert. That character he is playing is so moronic. That is what is so great about the piece. Dave is in the van and Rupert is being fed the lines. So you hear Dave say the line in the way that only Dave can deliver it. Then you hear Rupert say the line a second time, and that is what makes the piece so enjoyable: hearing Dave’s humor come out again in that earnest, flat tone. As a comedy writer, it is a great to have this vehicle that you can trust. It doesn’t matter what I write. If Rupert says it, Steve Young is gonna fall off the chair laughing.

Photo by Scott Ryan

Rupert Jee: I called that the suicide skit. I am all wired up with an earpiece and a camera. Dave would feed me these lines to tell people and tell me to do some crazy stuff. I still didn’t understand what was going on until we started to execute it. After one hour, I knew it was going to be something special. Rob Burnett and Dave have been around humor their whole lives. I never had seen them laugh or smile at anything. What I thought was funny they wouldn’t even laugh at. But I could hear them through my earpiece cracking up in the car. The fact that they were laughing at the whole thing was a testament to me that this would be a very special skit. 

Lee Ellenberg: You don’t have to have a killer joke, because you knew coming out of Rupert it was gonna play. I loved writing and shooting with Rupert. Dave is always big on when we were doing pieces that the joke was on us. You aren’t the idiot; we are the idiot—which is something that has changed in TV that I am not entertained by.

Eddie Valk: When I started off as a stage manager, I used to go into Rupert’s and let him know when he was gonna be on the air and made sure that the contestant knew what to do. I’d make sure the store was ready, organize the cue cards, and check the lighting—mostly make sure the shot looked good. 

Jeremy Weiner: Whenever we went to Rupert’s there was always a plan or quick game we could do with a pedestrian outside. The best was when we went out with a plan and then Dave went off script and went with his gut and just rolled with whatever was available out there.

Kathy Mavrikakis: Going into Rupert’s deli wasn’t a big thing from a production standpoint. We basically had an open-door policy with Rupert. I would work with my production coordinator and make sure I approved any additional crew members that we might need, like a new stage manager to be outside on the street all day. They needed my financial approval to do those things. 

Lee Ellenberg: I would get breakfast there. It was amazing. People go in and buy T-shirts and ask for pictures. And that is who that guy is. I like to think I am a kind, polite person, but here he managed to be this unfailingly polite and kind person to everyone. Every day for two decades someone would come in and they would tell him a story. He would appear to be riveted. That is why we all love the guy. Fame did not ruin Rupert.

Rupert Jee: It is still ongoing. It’s an experience that very few people have. I‘ve enjoyed it. I never expected it. It is fun and time consuming at the same time. You have to accommodate the tourist, but also tend to your business. But, hey, life could have been a lot worse. My only complaint is that Dave retired a little too early. Wait, I don’t want to burn the bacon. 

Rupert walks away to check on the bacon and begins waiting on a customer who has ordered the Paul Shaffer sandwich.

According to Worldwide Pants records, Biff Henderson was the third-longest-running employee. The only people who worked with Dave longer were Barbara Gaines and Jude Brennen. Over the years Biff went from stage manager to spokesperson for Dave. When Dave cut back on doing remotes, Biff stepped in. Whether it was spring training, Super Bowls, or small-town America—Biff Henderson was the traveling face of the show.

Lee Ellenberg: I remember Biff and I had to shoot a piece in Wyoming. We had to take a puddle jumper to get there, and we caught the flight at 4 in the morning. We shot in a town that had seventy people. It was really tiny. I lean back to sleep for the ride and I look over and Biff is talking to the guy sitting next to him, because even in this small town, the guy recognized Biff. That was surprising. 

Brian Teta: I actually spoke to him a couple months ago, which is great. I miss him a lot. Biff was absolutely the exact same guy on TV as he was in real life. He was a stage manager. People forget he was actually working. At a certain point, he became a bigger star than a lot of the guests on the show, which is crazy. Even if you weren’t a religious watcher of the show, you knew Biff Henderson. When he walked down the street, he would grumble when he couldn’t walk five feet without being asked for a picture, but I think he loved it.

Lee Ellenberg: Biff, a director, and a writer would go on the remotes. We would go out with two or three pages of jokes. Usually it was questions. It was always supposed to be an honest reaction from people attending the events. If the person said something amusing, then you could scribble something down on a legal pad and Biff could say it. It was a very primitive way that we went about filming those pieces.

Jeremy Weiner: I worked with Biff for many years. I used to travel with him on the “Biff Henderson’s America” or Super Bowl spots. Dave sort of transitioned out of doing remotes and that is when Biff sort of became the one that would go out and do “Biff Henderson’s Stopwatch.” 

Lee Ellenberg: When I’d do a Super Bowl piece with him, there were people everywhere and jumping in the shot. You’d say, “Biff, walk over to that mustard dispenser and do this.” You’d be surprised how many times you had to do that, because someone is calling out, “Biff!” or jumping into the shot. When I would shoot those with Rupert it was hard, but when it was Biff, he would be surrounded by people.

Randi Grossack: I was the director with Biff and Dave’s mom at the Olympics. I did the Super Bowl pieces every other year. I was especially proud when Biff got to touch the Super Bowl trophy before it got on stage. I got to travel the world shooting stuff. There were two A.D.’s on the show, so we rotated who would go out and shoot things with Biff or Rupert. You can’t be thankful enough for that. When we did the Biff montage, there were so many clips that I got to direct.

Jeremy Weiner: Lee and I worked on Biff’s montage. I had a lot of firsthand knowledge of things from 2000 on because I was working so closely with him. I needed to rely on Barbara, Kathy, Mike McIntee, and others to help me remember all the other stuff that Biff did. You couldn’t screen everything, so it was asking people for their favorites and then looking back at those. 

Lee Ellenberg: Randi and Jessica were in charge of footage and clips. Randi sent us a list of every remote. Jeremy and I checked off the ones that they should load into the Avid. When I got the job at Letterman, I was twenty-four. I had watched the show. So I knew who Biff was. He was a celebrity to me. 

Jeremy Weiner: Biff was so authentic. That is why he was so great on air. He was a straight shooter. He just had this presence about him and was always so genuine. That was what was great about Biff, Rupert, and all these people we ended up having on the show. They got used to being on camera a little bit, but they never really changed, and that was the best part. 

Writer Jill Goodwin with Biff Henderson. Photo courtesy of Jill Goodwin.

Rick Scheckman: Biff wasn’t a trained actor. He was beloved and very good on camera. That is what is so funny. Biff was lightning in a bottle. He would do almost anything you asked. His reactions were genuine, like when he shot that starter’s pistol early in the supermarket bagging contest. You would see him flinch. That was real. He is not acting. There was one show when we played “May We Turn Your Pants into Shorts.” He does this triple take because he didn’t want his pants cut. You can’t script a triple take.

Eddie Valk: Biff is one of the kindest men you’ll ever meet. I got my start as a stage manager because of him. I was a production assistant. I expressed to Jerry that I wanted to start stage managing. I started to fill in when they would write a segment for Biff to be a part of. They needed someone to replace Biff. So if it wasn’t for him, I wouldn’t have a career. When he was on camera, I would fulfill his duties as stage manager. From there I worked my way up. 

Brian Teta: My favorite Biff moment was when we had a phone in the airlock where you would page the guest to tell them they had to come down. There would be this massive star and he would say their names completely wrong. He could not have cared less. [Laughs] I would say, “That isn’t their name.” He would say, “Aww, shit.”