For 30 years Howard Stern has been a guest on Letterman's late night show. Whether it was on Late Night or Late Show, Stern’s common topics generally include therapy, sex, Paul Shaffer, and Jay Leno. Stern has been one of Letterman’s most engaging guests; he’s one of the few that overpowers Letterman and becomes the interviewer, usually making the host grimace. Stern is part of the elite group of guests that Letterman clearly likes having on — even if the conversation isn’t always to Letterman’s fondness. Letterman is like Stern's older brother who's disappointed yet always entertained. Stern has made over 20 appearances on Letterman’s shows and continues to be a regular on the Late Show — here are some of his most memorable appearances:
1984: Difficulty with management
In one of Stern’s first appearances on Late Night, Stern comes out, stands up, and takes a phone out of his pants saying “I can’t live a lie.” Letterman then throws the phone behind the window. Some of the highlights of the interview include Stern wanting a shot on Carson, Stern’s lack of intimacy with his wife, George Bush — “how does [George Bush] get worked up over Barbara Bush” — and his well-known issues with his bosses at WNBC.
1988: Underpants and Negligee party
Stern talks about the Underpants Party he’s throwing, how he wants to live like Elvis, his fight with Cher, and how he shouldn’t be “lumped in with other DJs.”
1991: “Maybe I look like an Elkhound, but I know what the people want”
Letterman and Stern discuss his mother and father’s sexuality, Stern’s elkhound look, and lesbians.
1992: “I never liked Johnny”
Here’s the first interview where Stern expresses his passion for the Late Night War and his dislike for Leno and Carson. Before Letterman poses a question Stern asks “How long does Jay Leno really have?” Stern mocks Leno’s theme song and calls Johnny Carson a “bore” then asks Letterman where he eats lunch with Carson. Stern praises his fans that make phone calls to live call-in shows and tells a story about upsetting Sharon Stone by calling her attractive.
1995: “You are, without question, the single ugliest lifeform.”
This is Stern’s most memorable Letterman appearance. Letterman introduces Stern as “America’s worst nightmare.” Howard Stern affirms this statement by coming out in drag to promote his book Miss America. In an attempt to get Letterman his best ratings ever he has two men kiss on the show. He also brings up lesbians.
1999: “You have been wasting away on Radio.”
In this interview Howard Stern strips down to his underwear, so Letterman then takes off his jacket in an attempt to cover up Stern. Topics in this interview range from fitness, Stern’s move to CBS, and how Stern forced the Goo-Goo Dolls to play music to men in thongs.
2004: “In five years satellite radio will be the dominant medium in radio broadcasting.”
This is one of Stern’s less comedic visits to Letterman. The two discuss Stern’s exit from terrestrial radio, the future of Satellite Radio, and the 2004 presidential election.
2006: Stern gives away free Sirius radio
Christmas-clad Stern comes out and gives free Sirius satellite radio packs to the audience. Stern discusses avoiding Gayle King and Al Roker and helping out a transsexual on his new show.
2009: “I didn’t like Jay, I never liked Jay, I can’t stand Jay.”
Stern talks about feeling the pressure to help Letterman beat Conan’s Tonight Show and his dislike for Leno’s last Tonight Show. Topics include why Richard’s Simmons never found the right woman, Stern and Letterman seeing therapists, and Stern’s talent for extracting sexual information from people.
2011: “When you had that Super Bowl commercial with Jay, we had the guy down on the ground.”
Stern compares his fascination with the Late Night Wars to studying Torah, then he tells Paul Shaffer he’s complacent.
2013: “I know I always bring up Jay Leno every time I’m on here.”
In Stern’s most recent appearance on the Late Show, Stern discusses how Stern feels like he’s fighting Letterman’s war while Letterman has been exchanging phone calls with Leno. Stern says Leno “snatched [Letterman’s] dream away.” The interview ends with Letterman and Stern dancing and Stern kissing Letterman’s hand — a fitting last appearance.