Madonna has always had a fond liking for dating men younger than her age, and the music star has dated several men, from actors/directors to dancers, who have massive net worths.

Madonna had always been interested in dancing and even received a scholarship to study the art form at the University of Michigan. She joined two bands, Emmy and the Breakfast Club, to hone her musical skills before venturing solo and signing with Sire Records. After her debut singles, Madonna became an instant hit. Her second album, Like A Virgin, made her the first female artist in history to sell over five million albums worldwide. Over the years, her music, visuals, and style have pushed the boundaries of traditional music and entertained audiences. Her popularity has always led to deep media scrutiny about her private life, and Madonna has had several high-profile relationships and marriages.

Madonna has been married twice, and the singer has since dated several men in her life. Often the people she has dated have been significantly younger than her causing curiosity about her relationships. Let’s look at all of Madonna’s boyfriends, ranked based on their net worths.

9 Dennis Rodman ($500,000)

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Madonna and Dennis Rodman had a highly publicized romance in 1994. According to Marie Claire, despite the long-term media scrutiny about their relationship, they only dated for two months. Rodman has detailed a good portion of their relationship in his memoir Bad As I Wanna Be. Roadman is a retired professional basketball player, a five-time NBA Champion best known for playing with the Pistons and Bulls. He made $27 million in NBA Salary during his career.

RELATED: Dennis Rodman Net Worth

8 Ahlamalik Williams ($500,000) S

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Ahlamalik Williams is a renowned dancer who has collaborated with various artists, including Nicki Minaj, and even released music through his collaboration with Stella McCartney. He is a part of the urban performance art group RAW By Nature and first met Madonna as a dancer on her Rebel Heart tour in 2016. The couple began dating in mid-2019 and broke up in 2022 after three years of romance.

7 Jesus Luz ($1 million)

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Madonna profoundly influenced and motivated her ex-boyfriend Jesus Luz for the better. As noted by Yahoo News, the pair began dating in 2010 and parted ways a year later. He detailed that she made him a better person and offered him life experiences. Luz hails from Brazil and is a well-known DJ and model. He began his modeling career at 19 and later became a professional DJ, making $15,000 per set.

6 Brahim Zaibat ($1.5 million)

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Brahim Zaibat is a famous dancer often spotted as a backup performer for artists on their world tours. Zaibat met Madonna in 2010 when he performed at her Macy’s clothing line launch party. The pair dated for three years, and Zaibat even worked as a backup dancer for her MDNA World Tour in 2012. After dating for three years, they parted ways in 2014, with Madonna dissing him on the song Unapologetic Bitch.

5 Dan Gilroy ($2 million)

 

Madonna and Dan Gilroy’s relationship dates back to when the singer was yet to skyrocket to fame with her music. She dated Gilroy for eighteen months, starting in 1979 when she was a drummer for the band Breakfast Club. Dan Gilroy was the band’s lead singer and even released a documentary, Emmy And The Breakfast Club, which has various footage of their relationship.

4 Carlos Leon ($5 million)

 

Carlos Leon is a notable actor known for his supporting roles in various television shows, including Nash Bridges, Oz, CSI: Miami, Person Of Interest, White Collar, and many more. Madonna began dating Leon in late 1994, and the couple had a three-year romance until they parted ways in 1997. They share a daughter Lourdes Leon who was born in 1996.

3 Vanilla Ice ($12 million)

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Vanilla Ice began his rap career in the late 1980s when he was signed with Ichiban Records. When he was 16, he wrote Ice Ice Baby but never released it. While performing a DJ set, he accidentally played the song, and the audience responded positively, making it a hit. As mentioned by InStyle, Madonna and Vanilla Ice dated in the early 1990s, and the rapper even referenced her in his music.

2 Sean Penn ($70 million)

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Sean Penn is considered one of his generation’s most successful actors and garnered two Academy Awards in the early 2000s. The actor has also ventured into directing and being an activist. Sean Penn met Madonna on her set of Material Girl in 1985, and the couple got married after dating for six months. Their relationship went through a tumultuous time, and they divorced in 1989.

1 Guy Ritchie ($150 million)

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Guy Ritchie and Madonna met in 1998, and within two years, the couple tied the knot in a private ceremony in Scotland. Their high-profile relationship was relatively private, and the couple had a son and adopted their second child. After eight years of marriage, the couple eventually split up, as stated by ET Online. Ritchie is a British film director best known for his gangster movies and the Sherlock Holmes series.

When asked why she dated younger men, Madonna candidly answered in interviews that the coincidence remains unintentional and believes that age is just a number. She enjoys being in fun relationships and her usual self behind the cameras. As Madonna broke up with her last boyfriend, Ahlamalik Williams, in April 2022, the legendary singer is currently single.

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Sources: Marie Claire, Yahoo News, InStyle, ET Online

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