Madonna's history of dating men decades younger than herself stretches back further than her current boyfriend, 30-year-old Akeem Morris, according to sources who spoke to the Daily Mail. Long before Morris, or even Carlos Leon, the father of her first child, there was Bobby Martinez, a teenage graffiti artist she met after moving to New York City in the early 1980s.
Morris was among the crowd cheering on the 67-year-old pop star at the FIFA World Cup halftime show in July, standing alongside several of Madonna's children, most of whom are closer to his age than hers.
A street kid from the Lower East Side
Martinez grew up on Manhattan's Lower East Side and was of Puerto Rican descent. As a teenager he was cast as an extra in the 1984 film Mixed Blood after being recruited by Lupe Garnica of CHARAS/El Bohio, a nonprofit community center for disadvantaged youth.
"There was a lady who was basically going to these people living on food stamps, giving them a chance to make some money as an extra in a movie," the film's casting director, Leonard Finger, told the Daily Mail. Martinez, also known by his graffiti tag "RP3," took a non-speaking role. Finger said Madonna was never on set, but that Martinez had reportedly begun getting close to the singer around the same time.
Introduced through Keith Haring
Around 1983, the teenager was introduced to Madonna by the artist Keith Haring, a close friend of hers. "Bobby, in his day, was like this absolutely gorgeous poster boy for what Keith's ideal was. Madonna's taste for young men at the time was exactly the same as Keith's. Young, Puerto Rican, hot, straight boys," said Gil Vazquez, Haring's longtime friend and former executive director of the Keith Haring Foundation.
"So what happens? Madonna enters the picture," Vazquez said. "The way Keith would tell the story is that Madonna 'stole Bobby' from Keith. It's hard to blame Bobby, it was Madonna. She's the hottest pop star in the world."
At the time Madonna was around 25 and riding high on hits including Borderline and Lucky Star. Sources differ on Martinez's exact age but generally agree he was in his mid-teens. In a 2015 interview on The Ellen DeGeneres Show, Madonna said, "When I moved to New York, I dated a 16-year-old," prompting DeGeneres to interject, "That was when you were, like, 18." In a February 1983 interview with Record Mirror, Madonna, then 24, said she preferred "effeminate looking men and young boys," adding that "15- or 16-year-old boys are best." Vazquez said the era's nightlife culture made such age gaps unremarkable at the time: "That was just sort of par for the course in New York City in the '80s."
On the set of Desperately Seeking Susan
Archival footage from the 1984 set of Desperately Seeking Susan shows Martinez standing close behind Madonna, smoking a cigarette and speaking softly to her before the pair walked out onto the streets of New York together. He is not credited in the film, suggesting he was there only to be with her.
That year, Madonna filmed the video for Like a Virgin wearing a belt reading "Boy Toy." Graffiti artist Cost, who knew Martinez personally, told the blog Vandalog that the belt was a nod to him: "Boy Toy was that guy RP3. He used to write Boy Toy and RP3, and that was her boyfriend at that time."
Andy Warhol's diary and Sean Penn's jealousy
Madonna's friend Andy Warhol also documented her relationship with Martinez in his diaries, writing that she was relieved her husband Sean Penn wasn't with her at the Mixed Blood premiere "so she could really have fun." Madonna and Penn met in January 1985 while filming her Material Girl video and married that August.
A 1991 Seattle Times report, citing Christopher Andersen's book Madonna Unauthorized, claimed Penn grew enraged over Madonna's continued closeness with old friends and lovers, and that "one night a jealous and intoxicated Penn stalked Madonna's old boyfriend Bobby Martinez with a gun." Martinez, interviewed for the book, said he was at the Palladium nightclub when he heard Penn was looking for him. "He walked up to the deejay and I was right behind him, but it was dark and there were a lot of people and he didn't see me. When he pulled back his jacket, I could see he had a gun," Martinez said. "So I got the hell out of there." Penn did not address the claims publicly, and his representative did not respond to the Daily Mail's request for comment. In a 2015 defamation trial involving director Lee Daniels, Madonna testified that Penn never physically abused her. She filed for divorce from Penn in 1987, and it was finalized in 1989.
A relationship that never fully ended
Madonna went on to date her Dick Tracy co-star Warren Beatty, whom she met on set in 1989, but sources say Martinez remained in the picture. Vazquez recalled a dinner around 1988 or 1989, also attended by Haring and stylist Maripol, where Madonna and Martinez were "canoodling." "It was the sort of body language two people have when there's intimacy," Vazquez said. Beatty's representative did not respond to a request for comment.
In his interview for Andersen's book, Martinez described the relationship's spontaneous, sexual nature: "We would get together at clubs, or we'd go to hotels. If she wanted to have sex, she'd say, 'Let's go f*ck,' and we did." Vazquez said that by then Martinez no longer resembled the "cute boy" of 1983 and 1984. "He looked like he had been through a few things. He was a little worse for wear," Vazquez said, adding he didn't know if Martinez struggled with drugs or alcohol. Martinez was never photographed with Madonna at award shows or on red carpets.
Haring's death and Martinez's disappearance
The dinner Vazquez described was the last time he saw Martinez and Madonna together. Haring died of AIDS-related complications in February 1990, and Martinez's life afterward became something of a mystery. A New York local who often saw Martinez at parties in the 1980s told the Daily Mail that many in Haring's circle were "getting sick and dying" around that time. "They were all dropping like flies. Some people disappeared, some people got sick. This Bobby kid, he wasn't famous. Anything could have happened to him," the person said.
Cost claimed in a 2012 blog interview that Martinez had in fact died, saying: "He ODed and he's been dead for a long time." It remains unclear whether Madonna and Martinez ever spoke again.
A lasting pattern
Since then, Madonna has dated a string of men significantly younger than her, including Leon, who is eight years her junior; Jesus Luz, 39; Brahim Zaibat, 29; Ahlamalik Williams, 31; Josh Popper, 32; and most recently Morris. "She's just been on this long string of guys that are decades younger than her, gorgeous. They're all, like, supermodels. And believe it or not, from what I hear, they are all totally into her, and they worship her," one New York insider said, adding that Madonna expects partners who "bring her flowers on a daily basis" and are available for "sex on a daily basis."
Madonna, who released the book Sex and the album Erotica, told the Daily News in 2015 that men her own age didn't interest her. "I'm a very adventurous person and I also have a crazy life," she said. "People who are older, and more set in their ways, are probably not as adventurous as someone younger."
Vazquez defended Madonna's preference, arguing it reflects a double standard. "Madonna has always behaved in ways that have been acceptable for men for decades," he said. "So the 60-year-old man dating a 24-year-old woman, it's par for the course for a rich, powerful man, but if she does it, it's taboo."
The Daily Mail has contacted Madonna's representatives for comment.
