Madonna has been known over the years for her sensational music, and her love life has not been a secret, either. To be precise, Madonna has been known for having the longest list of toyboys...compared to any other celebrity in Hollywood. She probably holds the record for ridiculous age gaps between herself and her lovers...only one has been older than her.

The rest?

Mostly more than a decade younger than her. Her latest one (just to point this out) is two years older than her eldest daughter.

In the spirit of toyboys, it's time to look at Madonna's relationships where the age difference thing was ridiculous – and some of her romances that were quite spot on. Read on.

20 Timor Steffens - 30 years

At the time that these two were hooking up, Timor Steffens was a youthful 26-year-old, trying his luck with Cupid...with a 56-year-old Madonna. According to Mail Online, the Dutch dancer and choreographer hooked up with the aging diva in 2014.

19 Guy Ritchie - 10 years

This is the man who managed to hold Madonna down for a while. According to Entity Mag, this might be the reason why Madonna commented that the marriage felt like a prison for the seven and a half years they were together. In her own words, she wasn’t free to be herself.

18 Vanilla Ice - 10 years

This rapper had his shot with Madonna for eight months back in the ‘90s. According to Entity Mag, the 24-year-old Vanilla then decided to call it quits...after Madonna released a book full of racy photos. He claimed that he didn’t want to be associated with that package.

17 Brahim Zaibat - 29 years

This was yet another of the more serious, yet ridiculously 'age gapped' Madonna relationships. According to Who’s Dated Who, Brahim Zaibat went from dancing on stage to sharing a bed with Madonna for three years, from 2010 to 2013.

16 Jesus Luz - 29 years

Right before Brahim danced his way into Madonna’s heart, another dancer, Jesus Luz, was enjoying the tunes. According to Mail Online, Luz, who was 21 then, had a significantly long stint with Madonna, stretching from 2008-2010.

15 Alex Rodriguez - 18 years

According to Fuse, this athlete's short fling with Madonna led to a divorce from his wife of six years in 2008. The 44-year-old baseball player, who was 33 then, dated the Material Girl from June to November of 2008.

14 Carlos Leon - 8 years

1994-1997 was the time frame when then-23-year-old Carlos Leon dated an eight years older Madonna...it was a relationship that graced them with their daughter, Lourdes. According to Mail Online, the two met in New York in 1994, before splitting seven months after the birth of their daughter in 1997.

13 Jenny Shimizu - 9 years

Jenny Shimizu admits to having a brief moment with Madonna in 1996, despite the Material Girl being 9 years older than her. According to New Theory, Jenny also admitted to wooing Angelina Jolie at the same time. Jenny and Angie also had a brief stint.

12 Tupac - 13 years

Yes. Madonna and Tupac were a thing. According to Mail Online, the two met in 1994, when Tupac was a young and vibrant 23-year-old. However, Tupac cut the cord in 1995, with a letter to Madonna (sent from prison) stating that he feared dating a white woman would jeopardize his career.

11 Jose Canseco - 6 years

Before Alex Rodriguez stole Madonna’s heart, another baseball player was about to hit a home run. Jose Canseco had a brief moment with Madonna in 1991 and, according to Fuse, the baseball player was married by then, with Madonna insisting he should marry her instead....and give her a child.

10 Tony Ward - 5 years

Before the Jose flop, Madonna was out hunting for another toyboy...this time, she chose a 38-year-old model, Tony Ward. According to Who’s Dated Who, the two dated from 1990 to 1991, before her head was turned by an attractive baseball player, Jose Canseco.

9 Lenny Kravitz - 6 years

Lenny Kravitz topped the list of Madonna's toyboys in 1990, for very wrong reasons. According to New Theory, the hit song, “Justify My Love”, had just been released when speculation about a Madonna-Lenny fling started up. That cost Lenny his marriage.

8 John F. Kennedy Jr. - 2 years

Yes. JFK’s son couldn’t keep his hands off the hot pop icon. And, according to Mail Online, his mother didn’t like it.

JFK Jr. and Madonna had their romance in 1988, with Madonna having been the huntress. Her friends claim that she expected an affair with the man to be nothing less than cosmic, using him as a rebound after her botched marriage to Sean Penn.

7 Jean-Michel Basquiat - 3 years

According to Mail Online, Madonna described the late Jean-Michel Basquiat as one of the few people she was envious of. They worked together at a time when the industry was predominantly white. Jean-Michel suffered from serious drug addiction, and an overdose of heroin claimed his life when he was 27.

6 John “Jelly Bean” Benitez - 1 year

Interestingly, these two had a stint between 1982 and 1985, with most people speculating that 1983 was the year that it all went public. According to Who’s Dated Who, this “IT guy” was THE mix master back in the 80s, having produced for big names such as Michael Jackson, Whitney Houston, and the sweetheart, Madonna, herself.

More interestingly, this guy was one year older than Madonna.

5 Sean Penn - 2 years

This is the most modest age gap you’ll see on this list. Sean Penn, who was aged 25 then, was Madonna’s first husband. According to Mail Online, the two hooked up in 1985, with the marriage lasting for four years before the two divorced in 1989. Sean was two years younger than Madonna.

4 Dennis Rodman - 3 years

Madonna and Dennis Rodman have had one of the most eventful relationships within celebrity circles. According to Entity Mag, this chap hooked up with Madonna in the mid-nineties and had the lass, who was three years older than him, beg him for babies.

3 Kevin Sampaio - 33 years

This might just be the biggest age gap we’ve ever seen in a Madonna romance. You’re in for a shock! According to Mail Online, the two have been linked together from 2017 until recently. Interestingly, he’s among the few individuals who’ve impressed Madonna (and earned her trust) for not going public about their relationship.

2 Ahlamalik Williams - 36 years

If you’ve been waiting for the bomber, then this is it. Madonna’s current lover is 25-year-old Ahlamalik Williams. To put the ridiculous age gap into proper context, this dude is only two years older than Madonna’s eldest daughter, Lourdes. According to Mail Online, the guy is a dancer and the son of a US military veteran.

1 Dan Gilroy - 1 year

This very short-lived relationship lasted barely through 1980. Dan, an American screenwriter, hooked up with Madonna back in their youth, a few years before she tied the knot with Sean Penn. According to Who’s Dated Who, the two ended the romance in November 1980, barely months into the relationship.

Sources: Who’s Dated Who, Mail Online, Fuse, Entity Mag, New Theory