On October 20 2005, Madonna was dared by David Letterman to get back on a horse – the first time since her fall (in August) which led to three cracked ribs, a broken collarbone and a broken hand. Madonna accepted the dare to ride again.
When asked why she hadn’t been on a horse since the fall, Madonna explained, “because my record company is not very keen on the idea of me injuring myself.”
On May 20 2015, Madonna acknowledged David Letterman’s retirement on Twitter:
@letterman Awww Dave I’m gonna miss you! Where am i gonna go on T.V. When I wanna say the F word? do you still have my panties???? this ❤#rebelheart loves you! – Madonna
On May 18 1994, Madonna made a surprise appearance on NBC-TV’s The Tonight Show, hosted by Jay Leno.
Watch this classic Madonna interview here:
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.