MADONNA's RELATIONSHIPS & COLLABORATORS

Madonna was a crucial part to my coming of age. Her music was the soundtrack to our lives for so many of my generation. She resonated with and spoke to "us" on so many levels. I've got a ton of memorabilia, autograph stories and even an in-person encounter, but I will talk about all of that separately. For the real nitty gritty and details on Madonna, I highly suggest "Encyclopedia Madonnica 20" by my buddy and Madonna uber-fan, Matthew Rettenmund. Also check out Matthew's very entertaining and nugget-filled blog www.boyculture.com He's got many great articles and stories in the same vein as bobbyatgloss; we get along like a house on fire, constantly sharing (often overlapping) celebrity stories and we both love to venerate the obscure. Thank you Matthew, for planting the seed and inspiring me to write my own blog!

For this entry, I want to focus on some of the men in Madonna's life. All these guys have had a connection to Madonna. One by blood, at least two romantically and the others who’ve been friends, in her videos and/or had Madonna contribute to their recordings.

Let’s start with the romances …

SEAN PENN AUTOGRAPHED PHOTO

When Madonna and Sean Penn were a couple, it was an absolute tabloid frenzy! Everything they did and everywhere they went was enthusiastically photographed, written about, praised, dissected and/or criticized (e.g., their movie “Shanghai Surprise). Madonna fans were torn whether this pair of powerful hot heads was a perfect match or if their relationship was a doomed volcano ready to explode. Of note is that I have ZERO photos of Sean Penn (at least, none that I could find) in my voluminous collection of hundreds of thousands of stills and photos. But I did have a complete file of newspaper clippings almost entirely devoted to his aggressive outbursts.

What a highly combustible couple they were – commanding unrelentless attention! Guests at their wedding had to experience a paparazzi nightmare! It was 1985, there were helicopters and clearly no drones or super cameras like we have today … but this video will give you the gist

TONY WARD NUDE MAGAZINES & AUTOGRAPHED SELf-PORTRAIT

Boy Toy indeed! Tony Ward had been a model long before he met Madonna and was already a part of the gay lexicon due to his nude magazine layouts featured in magazines like In Touch or Colt. As a couple, Tony and Madonna were strikingly complementary, she with her blonde locks and red lipstick and Tony with his dark, brooding good looks, great hair, and unique nose. Tony has subsequently done some work as an artist and photographer; I purchased a hand-signed print of his that was made in 2001.

Photogenically, Tony Ward and Madonna were magnificent together. I thought they were a great match and their combined sexual vibe shone in Madonna’s “Sex” book and in the “Justify My Love” video – a true art piece and one of her best videos and songs IMO.

CARLOS LEON AUTOGRAPHED INDEX CARD

When Madonna was with Carlos Leon, she appeared to be the happiest I had ever seen her. With Carlos nearby, whether in photographs or on camera, her smile seemed genuine and joyful. I always thought they were such a perfect match because Carlos seemed to bring out the sweetness in her. Although we never really know what goes on behind closed doors, you can clearly tell when a couple are in love. Carlos was with Madonna the night she won the Best Actress Golden Globe for “Evita”. She was literally glowing onstage, and her cup(s) overflowed. Not only was she accepting a Best Actress Award, but she was also in love with the man on her arm … AND she had recently given birth to her first child, daughter Lourdes. See Madonna and her baby-daddy on that magical evening in the clip below.

And now on to family. Oh, brother!

CHRISTOPHER CICCONE AUTOGRAPHED BOOK

Madonna’s brother Christopher was instrumental in supporting her during the early part of her career. Assisting, managing details, and generally tending and helping his sister navigate many details associated with a quick ascendancy to superstardom. The fallout between a brother and sister can be heartbreaking though. Maybe writing a tell-all about your super famous and powerful sister was not such a great idea. We will never know the true reasons why Christopher wrote “Life with My Sister, Madonna” (2008) and I do hope they had some mending of fences before he passed away in 2024. Let’s just remember when he was the helpful brother and being a back-up dancer for his sister performing “Holiday” (1982) on a television show.

Madonna’s career gets into the groove with some help from her friends …

PATRICK HERNANDEZ AUTOGRAPHED 12" SINGLE OF "BORN TO BE ALIVE"

One-hit wonder “Born to Be Alive” – that’s how I know Patrick Hernandez. But Patrick was one of the first people to give Madonna a break in the music industry. She was selected to be one of his back-up dancers on a worldwide tour on the heels of “Born to Be Alive” success. I’m not clear on exactly how many tour dates she performed, but it helped get her foot in the door. And oh yeah, she and Patrick dated. Note in the photo of Madonna and Patrick together how he has such a proprietary grasp on her and his dangling hand of "boob ownership". Watch this very young, dark-haired, boyish Madonna being a “back-up” (but in-front) dancer for Patrick.

JELLYBEAN BENITEZ AUTOGRAPHED LP

Jellybean was one of Madonna’s early boyfriends and career boosters. A successful DJ that played Madonna’s first single “Everybody” (1982) in the club, he was hired to remix several of her early singles and he produced her first Top Ten hit “Holiday”. Oh yeah, Jellybean and Madonna ALSO dated. She not stoopid. Jellybean asked for and got a favor from Madonna to sing on his 45 of “Sidewalk Talk”. When it was first released, I thought it WAS a Madonna record. But it is actually Catherine Buchanan on lead vocals, assisted by Madonna and released under the name “Jellybean”. Listen for yourself

THE MEN IN MADONNA'S VIDEOS

Madonna says: "Hey! Do you wanna be in my video or movie?"

DANNY AIELLO IN-PERSON SIGNED AUTOGRAPH

Yes, I know that Danny Aiello has a long and illustrious career in high profile movies and a slew of nominations. Because he was a great actor, of course. But he is forever etched in my memory from Madonna’s “Papa Don’t Preach” video. What can I say? I haven’t seen “Do the Right Thing” or “The Godfather Part II”. But I saw him in “Moonstruck” and Madonna’s video. Pair someone with a diva and “we” probably know him for that.

But here’s what DANNY said about “Papa Don’t Preach”: “You know, that came about in a very strange way,” Aiello said in 2017. “I had no idea who [Madonna] was, so I said to [daughter] Stacey in passing, ‘They want me to do this music video with this girl named Madonna.’ She said, ‘Dad, Dad, you have to.’ I went back and said I’ll do it if my daughter is permitted on the set taking pictures with Madonna.”

Stacey didn’t get what she wanted and she wasn’t happy. “Madonna sort of backed up and told her representative that I don’t do that,” Aiello recalled. “My daughter has hated her ever since … I’m a movie actor doing this piece of crap!”

I met Danny Aiello in person in 1993. He was appearing in “Breaking Legs” with Karen Valentine, Larry Storch, Harry Guardino (see him under Lauren Bacall) and Larry Storch. I had photos for Karen, Larry, and Harry – all of which they signed upon leaving the stage door. Harry Guardino signed my playbill also. And I waited patiently for Danny to come out; he seemed to take forever and then finally came out and very grudgingly signed my program. All I can say is either (a) he didn’t like to sign autographs, (b) he didn’t like me or (c) the dude was having a grumpy day. “I’m in trouble deep”. But I got a quick signature. It was driving me nuts that I couldn’t find the program, and then I realized that I sold it years ago. This goes to show either how (a) organized I am that I can find a photo in my eBay sold files from 2023 or (b) that I have GOT TO GET RID of so much clutter; physical and digital.

Anyways, luckily, I also have this great 8x10 also signed of a smiling Danny Aiello. And that’s how I would prefer to remember him.

LEON (ROBINSON) AUTOGRAPHED PHOTO

A sweet Pepsi commercial. Followed the next day by a video premier of “Like a Prayer” featuring an interracial kiss between Madonna and a black saint (Jesus?) played by Leon. The Pope’s has something to say. Pepsi stops playing the commercial because of the religious controversy. Madonna still gets to keep the $5,000,000 that Pepsi paid her. And Leon (Robinson) gets a lot of attention. (P.S. For fans of “Real Housewives of Atlanta”, you will have seen Leon on the show a few times as Cynthia Bailey’s ex and father of her daughter.)

The world was such a crazy place in the 80’s with zealots on all sides trying to cancel something or another. Oh, that’s right. We would never do stupid shit like that in 2025.

Now check out the Pepsi commercial seen by 250 million people and the “Like a Prayer” video that followed on the airwaves the next day.

CHRISTOPHER WALKEN SECRETARIAL AUTOGRAPHED INDEX CARDS

“Bad Girl” is one of Madonna’s best produced “short movie” music video. It has beautiful cinematography and contains some fine acting on Madonna’s part portraying a lonely, dissatisfied and danger-seeking woman a’la Diane Keaton in “Looking for Mr. Goodbar”. It also features one of Madonna’s during her most glamorous Marilyn Monroe phase on the CD and vinyl releases. The icing on the cake is Christopher Walken as either her guardian angel or the angel of death watching the entire scene unfold. I think the video is a masterpiece – and Walken is always so effin’ good. I’m sorry to say that both autographs in my collection of Christopher Walken are NOT so effin’ good – they’re both forgeries. (Just to help you fellow collectors know what not to look for!)

RUPERT EVERETT AUTOGRAPHED PHOTO & INDEX CARD

“The Next Best Thing” was perhaps not. But it DOES have two good things. Handsome Rupert Everett during his prime and a soundtrack that includes Madonna’s version of “American Pie”. Here’s my favorite mix:

ROBERT WUHL IN-PERSON AUTOGRAPHED PHOTO

In the beginning of Madonna’s “Material Girl” video you see Keith Carradine and a “yes” man watching her on screen. The “yes” man was Robert Wuhl, who I met in May 2025. Sitting at his table with a lot of photos from his “Batman” role, he was extremely business like. He was fitter than I expected and had a very firm handshake. “I’ve never seen this before”, he said about the composite photo I had made from the video. He inscribed as I requested and accepted a copy of the picture but did not offer me a discount in exchange (as many do when I give them a shot they don’t have).  It was $40 for the autograph. It was purely transactional, with no commentary or back-story. He didn't seem interested in discussing the “Material Girl” video or Madonna since he made zero comment on the inscription that I requested: “The biggest star in the universe. Right now as we speak!” After he signed, I wanted to ask some questions, but he turned away and started talking to somebody else. Dismissed. The creator of “Arliss” was not there to gossip about Madge.

HARVEY KEITELAUTOGRAPHED PHOTO

I love Madonna's music. I like some of her movies. I did not see "Dangerous Game" with Harvey Keitel. Re-watching the trailer in 2025 and checking out reviews to see if they've gotten better over time, I think I'll stick with "nope". Still nice to have Harvey Keitel in my autograph collection though.

MADONNA'S MALE PROTEGES

Madonna helps boys singing careers -

NICK SCOTTI AUTOGRAPHED PHOTO & INDEX CARD

Male model gets Madonna’s attention. Huh? What? When does that ever happen? He gets a deal with Reprise Records, Madonna writes and sings backup on a song for him, he reaches the Top 40 Dance charts with two singles and never releases a second album. He did, however, make a popular gay movie called “Kiss Me Guido”. And he was playing Words with Friends with me for years. I think. Do we believe anybody’s profile picture and online name? Male model gets Madonna’s attention. Huh? What? When does that ever happen? He gets a deal with Reprise Records, Madonna writes and sings backup on a song for him, he reaches the Top 40 Dance charts with two singles and never releases a second album. He did, however, make a popular gay movie called “Kiss Me Guido”. And he was playing Words with Friends with me for years. I think. Do we believe anybody’s profile picture and online name? Here's a great remix where Madonna's vocals dominate Nick's #33 Dance Club Play hit “Get Over”

JOSE & LUIS "THE QUEEN'S ENGLISH" LP & CD

There was a time when Jose Gutierez and Luis Camacho were constantly at Madonna's side, it seemed. In the "Vogue" video and "Truth or Dare" documentary, on the "Blonde Ambition Tour", in magazines with her on the red carpet, etc. "Oh, how to be in Madonna's inner circle like those two guys!" They were able to parlay their Madonna connection into a few songs on "New Faces". And Madonna pitched in with background vocals on their song "The Queen's English". Both the CD and 12" are becoming more and more collectible. Get yours now. Not sure why there isn't a higher quality version of their video available, but here it is. It's a fun time capsule and always nice to hear Madonna pitch in.

NICK KAMEN AUTOGRAPHED LP INSERT & VINYL COLLECTION

Such a beautiful man!  Nick Kamen started out as a model and really got attention with his Levi's 501 commercial where he strips down to his underwear in a laundromat.  I think this helped get Madonna's attention ... perhaps?

Regardless of how they met, Madonna wrote, produced and sang backup on Nick Kamen's first hit record "Each Time Your Break My Heart".  Obsessed with everything Madonna, and hearing her on background vocals, plus the photo of her on the back of the 12" ... I started following Nick Kamen's career also.  He was just so uniquely handsome and eye-catching with a smoldering public persona.  Here he is performing (lip-syncing) on foreign TV - see his visual appeal in all its glory!

Nick Kamen was pretty popular in Europe and had some mid-charting songs; a few of which are quite poppy and fun.  It's his IMAGE and the picture sleeves, album covers and promotional materials that are outstanding and so attractive to collectors.  As you can see, from my collection his record companies knew how to market Nick and they didn't scrimp on the photo sessions!  If you are not familiar with Nick's songs, I strongly recommend the beautifully packaged and lovingly assembled boxed set of all of his albums - each CD in the set has a sleeve which is the original album cover and the liner notes are great.  Nick Kamen died at the age of 59 of bone marrow cancer - very sad.  By all accounts, he was a kind and gentle person - Madonna posted a lovely tribute when he passed.  Nick Kamen made just a dent in the music world, but he will always be a favorite of mine.

P.S.  Levi's hired Beyonce to recreate HER version of Nick's 501 commercial.

I'm curious to know how many views occurred on NICK'S version when the Beyhive swarmed into the details behind the "Launderette"

P.S. There's a laundromat in Burlingame that holds a special place in my heart. For it was there, in my quest to have someone watch my laundry, that I made a special friend, Elaine A. Many years, joints and big smiles later, I'm happy that we are still in touch. You just can't make new old friends. Especially during the drying cycle.

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