10 Of Hollywood's Most Notorious Bachelors

Who are the most notorious bachelors in Hollywood? Furthermore, what makes a bachelor notorious? Every time a notorious bachelor dates a new girl, the tabloids follow them around like bloodhounds with cameras (if dogs could shoot candid pictures, that is). You can’t miss headlines like, Will She Finally Be The One? or Handsome, Smart, Rich Star Dates Hot, Sexy A-List Lady. Here are ten of Hollywood’s most notorious bachelors. The question isn't who they will settle down with, but if they will ever settle down at all. Do they even need to? Maybe they just need to find a notorious bachelorette to seal the deal with…

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10 Leonardo DiCaprio


9 Bradley Cooper

8 Taylor Lautner

Twilight werewolf and hottie Taylor Lautner, has been dating actress Marie Avgeropoulos since 2013, but he hasn't exactly gotten down on one knee just yet. Prior to Marie, he dated Taylor Swift. In fact, their breakup inspired the song Back To December. While they dated, they were known as Taylor Squared, which would have been cute, but alas, it was not meant to be (we probably could have guessed that). Before Swift, he dated actress Selena Gomez, who in her case, has been on and off with Justin Bieber ever since.

7 Jake Gyllenhaal

When will Jake Gyllenhaal ever find the right girl? Currently, he has been dating actress Rachel McAdams since the summer. Previously, he dated a slew of women including Reese Witherspoon, Jenny Lewis, Natalie Portman, Kirsten Dunst and Anna Kendrick. He also dated the most notorious bachelorette in the world, Taylor Swift. He even inspired her hit song, We Are Never Ever Getting Back Together, which proved to be true. The actor also inspired the songs Maple Lattes, Red and State of Grace. Unfortunately, their breakup wasn't so graceful. Gyllenhaal’s sister Maggie has been happily married to Peter Sarsgaard since 2009, so maybe there is hope for him. No matter what, he won’t have a shortage of interested ladies.

6 Tim Tebow

Former New York Jet and Denver Broncos Quarterback, Tim Tebow is the most religious bachelor on this list. At 27 years old, he is reportedly still a virgin. Tebow has been rumored to have dated some of Hollywood’s most notorious bachelorettes, including Taylor Swift (but she’s dated everyone, including several people on this list), Dianna Agron, Camilla Belle, Lindsey Vonn (who ended up dating Tiger Woods, who is the opposite of Tebow in every way), Katy Perry, Kate Upton, and Lolo Jones. His latest girlfriend is rumored to be no other than another Christian virgin, 19 Kids And Counting star Jana Dugger. Out of all the women on this list, it sounds like Dugger is probably his best match.

5 Drake


As a man, Drake has so much to offer. He’s half black, half Jewish, 100% Canadian and 1000% hot. The rapper has dated Rihanna on-and-off, for nearly four years. When RiRi was off with Drake, she was on with Chris Brown. Drake has also dated the beautiful Amber Rose, and the butt-tastic Nicki Minaj (but we like him with Rihanna so much better). Drake also apparently has a thing for cougars, having been rumored to date Rashida Jones and Tyra Banks. He also dated rock royalty/actress Zoe Kravitz (daughter of Lenny Kravitz and Lisa Bonet). The rapper seems like such a nice guy, hopefully he will settle down with a nice girl sometime soon.

4 Russell Brand 


3 John Mayer


Who hasn’t John Mayer dated? Mayer used to date Jennifer Love Hewitt, who is the subject of his hit song, Your Body Is A Wonderland, but their relationship wasn't so wonderful. Mayer also dated Jessica Simpson, Minka Kelly and Jennifer Aniston. Of course he dated Taylor Swift, and considering their careers, they seemed like a good match from the outside, but we all know Tay Tay goes through boyfriends like shoes. At least she was able to write the songs, Dear John and I Knew You Were Trouble about it. His most recent girlfriend is the former Mrs. Russell Brand, Katy Perry. However, they split up earlier this year, reportedly due to his infidelities.

2 Prince Harry

Who wouldn't want to marry a prince? While he’s British royalty, Prince Harry is still one of Hollywood’s most notorious bachelors. Why? He’s hot, sexy and most importantly, the wildest prince in the land. For years, he dated Chelsy Davy on-and-off again, and even took her to the Royal wedding. However, she said she would never marry Harry because “it’s not a life for me.” Currently, Harry is rumored to be dating another on-again off-again girlfriend, Cressida Bonas. They were spotted in September at a movie together. The movie was Sex Tape, which is ironic because the prince is rumored to have filmed one.

1 George Clooney

George Clooney is married now, but the former Sexiest Man Alive was one of Hollywood’s most notorious bachelors for years. Many people forget that Amal Amuddin is actually Clooney’s second wife. From 1989-1993, he was married to actress Talia Balsam. Post divorce, he dated Céline Balitran, Krista Allen, Elisabetta Canalis (who then went on to date Steve O from Jackass, which was a definite downgrade), and former wrestler, Stacey Keibler. There were many rumors he was going to marry all of these women, but he preferred the bachelor lifestyle. That was until he met Amal Amuddin, who looks like a model or movie star, but is actually an attorney. Perhaps this is a lesson all the bachelors on this list can learn- sometimes, you just have to find the right woman.

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