It’s always an adventure when Madonna sits down with Jimmy Fallon on The Tonight Show and Wednesday night’s (Aug. 10) whirlwind couch trip was no exception. The pop high-priestess came fully loaded with provocative schtick, from showing off her glittering “birthday grillz” — in advance of her 64th birthday next week — to gifting a nervous Fallon with a tiny, sassy handbag and roping him into a PG-13-rated alphabet guessing game.
Ostensibly in the house to promote the upcoming 50-track version of her dance remix collection, Finally Enough Love: 50 Number One (Aug. 19) — which features such guests as Justin Timberlake, Britney Spears, Nicki Minaj and Maluma, among others — Madonna revealed to Fallon the one artists she hasn’t yet collaborated with who’s at the top of her wish list.
“I mean there’s one artist that I worship more than anything in life and I would love to collaborate with him and that’s Kendrick Lamar,” she said. “His new record is, like, history-making… mind-bogglingly brilliant,” she added about K-Dot’s Mr. Morale & The Big Steppers.
Diving into the history of her record-breaking string of hits, Madonna recalled her early days at New York’s legendary Danceteria nightclub in the early 1980s, when she had to “promise everything” to the club’s DJ to convince him to play her song “Everybody.” When he did, she recalled, “everyone got up and started dancing to it and it blew my mind.” They also touched on “Like a Virgin” producer Nile Rodgers disagreeing with releasing that song as a single in favor of “Material Girl.”
“Those were the days when I had no say in anything. Can you imagine those days even existing,” she said with a smile, noting that she thought the song might be too controversial to get on radio. “It wasn’t the song itself, it was my performance on the first MTV Awards,” she recalled of her slow walk down the stairs of the steep cake-like set in a puffy wedding dress in 1984. “I got the bottom and I started dancing around and my white stiletto pumps fell off.”
Attempting to save the moment while diving for the shoes and trying to make it look like planned choreo, the singer’s dress “flipped up” and the audience got way more than they bargained for. “My butt was showing. Can you imagine? Those were the days when you shouldn’t show your butt to have a career. Now it’s the opposite,” she said.
Even though it was really only the one cheek, when she left stage her manager at the time told her that her career was over because of the incident. Not by a long shot, as it turns out.
When Fallon asked about her 16-year-old son, David, she said he would have totally been on hand to hang with his favorite late night host if not for a boxing lesson. Madonna also noted that aspiring musician David has so much swag that he can wear any of her clothes and make them look way cooler. “It’s really irritating. He wears my clothes and looks better in them,” she complained. “He can even wear a dress and look butch.”
Speaking of butch, Madonna busted out a special gift she brought along for Fallon, a tiny, glittering handbag that read “butch,” which Jimmy proudly strapped across his chest. “This is so cool,” he said. “‘Watch out, Butch is comin’ through!'”
The singer also played the “Naughty Word Game” with Fallon, a contest of her own making that made Jimmy anxious just thinking about it. To Fallon’s mock horror, the singer managed to find every possible dirty word to go with her half of the alphabet, warning Fallon not to censor himself. “Oh my God, I got a P!” she said with a snicker on the first flip, later suggesting the host swap “Madame X” for “X-rated” when he turned over the 24th letter.
In addition to a spirited revival of the pandemic-delayed “Classroom Instruments” segment, naturally, her visit ended with Fallon lying on his stomach on the floor as Madonna climbed aboard and pretended to ride him like a pony.
Check out Madonna on The Tonight Show below.