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The 50 Biggest Mama’s Boys Ever

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Mother’s Day is on its way. Did you pony up for a gift yet? No? It’s cool, she only gave you the gift of LIFE. No, not the magazine.

No matter what kind of relationship you have with your mom, as men we have to give it up for the fairer gender. Pushing a bowling ball out of you isn’t enviable – remember your bout in the bathroom after eating that Grande Burrito Platter? However, some guys take their appreciation, fondness, and love for their mothers to another level. Some would call those dude ‘Mama’s Boys’, which is a term that’s been interpreted differently since its inception.

Originally, it was defined as a man who is excessively attached to his mother at an age when men are expected to be independent. It’s often seen as a sign of weakness as the mom controls the son, but the son sacrifices that autonomy in exchange for the security blanket it provides. No matter how this relationship (and the man himself) could develop, it is generally believed a mother’s boy cannot maintain a healthy partnership with a woman.

Why the long winded explanation? Well, in honor of Mother’s Day, we’ve compiled a list of the 50 biggest Mama’s Boys. As you’ll see, the group is diverse – we have guys from all different backgrounds, some of which aren’t even real. Sports figures, comedians, musicians, historical figures, and figments of someone’s imagination – each belongs for one of the reasons we’ve outlined above.

Seeing the names we’ve gathered, maybe being a Mama’s Boy isn’t such a bad moniker after all?


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The smooth R&B singer – and infrequent actor – grew up with his mother, then-stepfather, and half-brother after his pops left when he was just 1. His mom eventually left her job to manage him for a stretch before Usher said, “YEAH!… that’s enough” in 2007. Often in mama’s boy scenarios, the mother believes there’s not a woman on Earth who is good enough for her boy. Usher’s mom didn’t even attend his wedding because she disliked his fiancee so fiercely.



The world’s most dangerous secret agent is egotistical and self-serving, which is a result of his tumultuous upbringing courtesy of his hot-and-cold (and mostly absentee) mother Malory. Oh, did we mention his middle name is Malory? Odd, right? Like most Mama’s Boys on this list, he doesn’t know who his father is and beds women like clockwork.




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Leo’s parents divorced when he was only 1, leaving him to live mostly with his mom who had to work several jobs to support them. Leo often treats his mother to lunches, dinners, and vacations and she often accompanies him as a date to high profile events – a common occurrence on this list. We don’t even have to mention the women he’s run through.


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The more talented half of ‘Kimye’ was three when his parents divorced, causing him to move with his mother to Chicago. Though his mom was a professor and chair of English departments at two different universities, she gave it up to manage Kanye. Unfortunately, she passed away in 2007. For all you Kanye fans, you might remember one of Mr. West’s tracks purportedly titled, “Mama’s Boy” leaked online. As it turns out, the single was actually titled, “Mama’s Boyfriend.” Regardless, either title would’ve worked as Kanye’s lyrics describe his feelings as a kid of divorce, watching his mom date multiple dudes, then his realization that he’s become one of those guys. He IS his mama’s boyfriend.


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The four-time series champion and three-time Daytona 500 champion admitted that his mom played a key role in developing his skills as a driver (a WOMAN knows how to drive!?!?). Turns out his dad would put her out in a car so Jeff could practice getting around her. That makes more sense. Here, the term is more about Jeff’s predilection for whining and nit-picking about his more lackluster results. Maybe he should just blame his mom for not pwning the track like Jimmie Johnson, Tony Stewart, and Kyle Busch.



The young womanizing nobleman from Florence was living the good life before conspirators took the lives of his father, and both his brothers, leaving only his mother and sister. His mom’s so traumatized that she loses the will to speak so in between missions Ezio spends his time collecting feathers and whatnot to cheer her up. Awwww.


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The Golden Globe winner is once-divorced and has two kids with two different women in addition to making a sex tape with Playboy Playmate Nicole Narain that never saw the light of day thanks to a lawsuit. Dude! His mom served as his date to the Oscars in 2008 and he’s full on admitted he’s a mama’s boy.


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The 14-time All-Star and all-time home runs leader* has been the subject of ridicule on countless occasions for his femininity, which most believe is a result of the steroids he allegedly took.


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Hitler’s dad was abusive, so he gravitated to – and found comfort in – his overindulgent mother who almost never disciplined or punished Adolf and often spoiled him. It’s been reported that when she died, the attending doctor said he had never known a son so full of grief over the death of his mother. The guy responsible for murdering millions of Jews kept his mother’s picture with him and often ‘gazed’ upon it. So, ya know, if you’re a father, just… take it easy, okay? This is the dark side of babying your son, moms.

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