On August 16 1985, Madonna and Sean Penn were married at a clifftop mansion in Malibu, California. Their wedding day was also Madonna’s 27th birthday.
Some of the celebrities attending the wedding included Rosanna Arquette, Tom Cruise, Andy Warhol, Cher, Martin Sheen, Rob Lowe, Carrie Fisher, Diane Keaton, David Letterman, Rosanna Arquette, Christopher Walken, Steve Rubell and many others.
Sean and Madonna later honeymooned at the Highlands Inn in Carmel, California.
Andy Warhol recalled this about the wedding:
It was just the most exciting weekend of my life. Martin went down to the hairdresser earlier in the day to have his hair done. We rode in a limo out to Malibu and when we saw helicopters in the distance we knew we were at the wedding. Somebody had tipped the reporters off about where the wedding was and about ten helicopters were hovering, it was like Apocalypse Now. And one helicopter had a girl hanging off with a camera and they were all trying to get in close. And the security people found camouflage-outfitted photographers in the bushes. And I looked really close at Madonna and she is beautiful. And she and Sean are just so in love. She wore white, and a black bowler hat, I don’t know what that was supposed to mean. And someone said that Sean had shot at the helicopters the night before. The only boring celebrity there was Diane Keaton, really. And it was the right mixture of nobodies and celebrities. Sean came over to say hello, and the good-looking family of Madonna was there, all the brothers. And you can see Madonna and Sean love each other so much. Really, it was the most exciiting thing ever.
On April 12 1994, Madonna sent a handwritten note to David Letterman wishing him a Happy Fucking Birthday.
The letter – sent less than two weeks after her infamous profanity-laced appearance on the Late Show – teasingly takes Letterman to task for having used the controversy to his advantage.
On February 13 1995, Madonna made a surprise appearance on CBS-TV’s Late Show with David Letterman.
In her first visit back to the Ed Sullivan Theater after her controversial 1994 appearance, Madonna presented Letterman with a Valentines Day gift.
And no, it was not her underpants…
On November 26 2003, Madonna appeared on The Tonight Show (with host Jay Leno) at NBC Studios, in Burbank, California.
Madonna handed out gifts to new dad David Letterman when she appeared on the Late Show earlier in the month, and she didn’t want to leave his TV rival Leno out.
“I brought you some Thanksgiving presents.”
Madonna handed the TV host a baseball jersey and a framed illustration from her new children’s book Mr. Peabody’s Apples.
Most odd about this appearance is that Remixed and Revisited was released on November 24 and Madonna never mentioned it. The Nothing Fails single was also released on November 21, and an upcoming single for Love Profusion (December 8) was also never mentioned. Very few artists would skip mentioning new releases in such a high profile interview. It makes me wonder how involved Madonna was with these releases – or if Warner Bros. was forcing the singles and the remix collection to be put out. All Madonna chose to talk about was her marriage to Guy, her father’s winery, her children’s books and Kabbalah.
For the record, I think this is an adorable interaction between Madonna and Jay. She’s funny, sweet and articulate.
On November 3 2000, Madonna guested on CBS-TV’s Late Show With David Letterman to promote the Music album. She performed an acoustic version of the album’s second single, “Don’t Tell Me.”
The performance featured several firsts for Madonna: her first live performance to promote the Music album; her first TV appearance following the birth of her son Rocco; her first performance on guitar since her pre-fame days in NYC band Emmy; her first unplugged/acoustic live performance; her first live performance with longtime guitarist Monte Pittman; and her first (and only) musical performance on the Late Show.
Despite being promoted as such, it was not, however, Madonna’s first time back to the Late Show after her infamously censored 1994 appearance. She had made a brief, unscheduled visit to the set to drop off a valentine for Letterman during a 1995 taping of the show.
On September 8 1994, Madonna presented the award for Video of the Year at the MTV VMA’s. She was escorted onstage by David Letterman, poking fun at their supposed feud following Madonna’s infamous profanity propelled appearance on Letterman earlier that year.
The appearance was intended to generate buzz for her soon-to-be-released single, “Secret” and its accompanying album, Bedtime Stories.
On July 1 1988, Madonna made a surprise unscheduled appearance on NBC-TV’s Late Night With David Letterman. Sandra Bernhard was David’s scheduled guest.