11 best moments from Madonna’s historic Howard Stern interview

The world turned upside down on Wednesday with Madonna's first-ever appearance on “The Howard Stern Show,” and while it wasn't the “gay Super Bowl,” as Bravo host Andy Cohen termed it (maybe a tad hyperbolic there), it was pretty surreal to hear the Queen on Pop in conversation with the King of All Media after so many years (decades, really) of seemingly mutual distaste.

So how did it go? I'm a little mixed, to be honest. While Howard was typically insightful as an interviewer, Madonna never really let her guard down enough to show a side of herself we hadn't previously seen.

Still, there were good moments. Here are ten highlights from the epic 90-minute sitdown, which included discussions of Madonna's childhood, her early New York years, past relationships with luminaries like Sean Penn and Warren Beatty, and her infamous fall at this year's BRIT Awards.

1. Baba Booey is shockingly good at guessing Madonna songs

Okay, so this isn't from the interview itself, but who knew Gary was such a Madonna fan? The show's producer revealed a surprising familiarity with the singer's music during a lightning round of “Name That Tune” with Howard in the lead up to the interview; he did miss one or two, but still, it was an impressive showing.

2. Madonna keeps them waiting

A lot of the thrill here was in the anticipation of Madonna's arrival — and boy did she take a long time to arrive. Not only did the show air six hours later than normal to accommodate her schedule — can't remember the last time that happened, if ever — but she didn't show up until at least two hours into the episode, after what appeared to be a lot of behind-the-scenes wrangling to actually get her into the studio. “Let's get Madonna in here, what are we doing?” Howard asked at one point with a hint of annoyance. And later he griped, “By the time she gets in here she's gonna have to leave.” All the stalling felt like a bit of a move on Madonna's part, but in a way it was the right one for an interview that proved to be such an event for fans of both entertainers.

3. That bizarre accent

I feel like I've heard a lot of different Madonna accents over the years, but I was almost startled by the one she brought into the studio today. Honestly, what was that affect? Had no idea she was Barbadian.***

4. The revelation that she dated Tupac Shakur

In the midst of discussing her infamous 1994 “Letterman” interview, Madonna casually mentioned that she was in a relationship with the rapper at the time: “I don't know, I was in a weird mood that day,” she said of the appearance. “I was dating Tupac Shakur at the time, and the thing is he got me all riled up about life in general. So when i went on the show I was feeling very gangster.” Though she claims the relationship was already known to folks “in the know,” it came as news to Howard, Robin and I'm sure a lot of listeners (including myself).

5. The portion where she talked about her mother's death

I'm sure diehard Madonna fans have heard her speak about this a million times before, but for someone who isn't as well-versed on the singer's past it was revealing to hear her talk about her mother's untimely passing by describing the way her father reacted (or didn't react) to it. “He never said how do you feel about it, we never had a group hug, we never had a cry,” she said. “My father's very stoic and old school….I don't think he had words for his pain.” For someone who's remained icy and unshakable in public life for over three decades, the brief tidbit provides a lot of insight into how she's managed to survive through so much career turmoil without breaking. Not to get too psychoanalytic, but compartmentalizing her emotions is a skill she seems to have learned very early on.

6. Her harsh thoughts on small town America

“I can't be around basic, provincial thinking people,” she said on the topic of leaving her Michigan hometown for New York City. I guess we've heard this kind of thing from her before, but it's still a pretty telling statement on her feelings about “everyday” humans. Then again, it's the kind of harsh sentiment her fans seem to eat up; for a mainstream entertainer in our “stars, they're just like us” age, she can be startlingly, aggressively inaccessible at times.

7. When she talked about former boyfriend Jean-Michel Basquiat

Madonna dated the late artist for a brief period in the early 1980s, and it was interesting to hear her describe how, upon breaking up with him over his heroin use, he demanded she return all the paintings he had given her before defiling them: “I loved him….when I broke up with him he made me give them all back to him, and then he painted over all of them black.”

8. The stuff she said about astrology

“I believe it's a science,” she told an incredulous Howard. “I respect it, yeah…[but] not the stuff you read in the New York Post!” Had it been anyone but Madonna saying this, I'm reasonably certain Howard's head would have exploded.

9. When she discussed her BRIT Awards fall

“The first thing that flashed through my mind was, 'I've gotta start this all over again,'” she said of her nasty tumble at the U.K. ceremony. “And then I realized it”s live TV…then I just danced like an angry matador for the next 30 seconds.”

10. When she basically took credit for inventing reality TV

“Don't you think 'Truth or Dare' was the start of reality television?” asked Howard. “”It absolutely was,” answered Madonna. There, done.

11. When she talked about preparing for her Super Bowl halftime show

For someone who so flawlessly projects confidence as a performer and rarely shows her vulnerable side, it was interesting to hear Madonna describe her wracked nerves in the leadup to her Super Bowl halftime performance: “Oh my god, I was so nervous. Shitting myself,” she said. And after it was over? “I was so relieved…that I went to my locker room, lay down on the floor and cried.” For the first time.

*** In fairness to Madonna, there are two factors that may have contributed to this: a) her cold and b) the fact that she was wearing a grill, both of which were pointed out in the course of the interview. (UPDATED 3/12, 11:09am PT)