15 Hollywood’s Hottest Cougars

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5) Madonna

Wow, what can we say about Madonna? Madonna is in her mid-50’s, so she’s a tad bit older than the conventional cougar, but she’s dating someone that’s more than half her junior – French break dancer Brahim Zaibat.

In fact, Madonna has made it a habit of dating men who are significantly younger than she is for pretty much her entire life (or good chunks of it at least), so she’s in a class of her own when it comes to being a cougar. Like in 2009 after her marriage to Guy Ritchie fizzled when she began dating then-22 year-old model Jesus Luz for a couple of years. Of course, after failed relationships with older and similarly aged men such as Sean Penn, Dennis Rodman, Warren Beatty, Vanilla Ice, Willem Dafoe, Jose Canseco, Big Daddy Kane, Antonio Banderas and John F. Kennedy Jr. (the list goes on and on and on, but we’ll stop there for the sake of space), who could blame the pop starlet for looking more toward younger men – she’s still got the goods to back it up. But Madonna had better watch out – one of her beaus might eventually flip-flop and have eyes for her teenage daughter, who is soon to enter college. Now wouldn’t that be something?