Regretful Morning

7 of the Luckiest Men in America

Posted March 11th, 2010 at 12:09 pm by

Some guys have all the luck. While most men bust their asses to get ahead in life, some men have been fortunate enough to achieve the dreams of many, while doing very little. This can be anything from becoming famous, earning lots of easy money, or sleeping with a woman that is way out of their league.

Now this list doesn’t include people who have truly earned “the good life.” You won’t see guys like Tom Brady or Justin Timberlake on this list because they have talent and have worked hard to achieve fame, fortune, and an endless amount of pussy. These are simply men who have no business being in the position they are. These are some of the luckiest men in America.


Seal is one of the ugliest people you’ll ever see. He suffers from a disease called Discoid Lupus Erythematosus (DLE). Because of this he has scars all over his face (and probably other places too). He had one hit song in the 90’s and he managed to turn his 15 minutes of fame into a lifetime of bliss with supermodel Heidi Klum. Now he probably does nothing all day but fuck Heidi and cash her Project Runway checks. It just goes to show you that even if you’re ugly, you can still get laid. You just have to have a nice singing voice…or you could be blessed in another area like the next person on the list….

Ron Jeremy

If you didn’t know any better, you might mistake Ron Jeremy with Khalid Sheikh Mohammed, the hairy-backed terrorist behind the World Trade Center attacks. Instead, he is a porn legend who has fucked thousands of beautiful women in his day. According to Wikipedia he has appeared in over 2,000 adult films and has probably banged just as many women off camera. He’s probably having sex as I type this. This guy is so ugly he makes Seal look like Tyrese. I can’t even watch porn with him in it because I’m constantly distracted by his disgusting body. I know he’s well endowed but I can’t believe this guy is considered the greatest male porn star of all-time.

Lil’ Wayne

Don’t EVER give up on your dreams folks. If Lil’ Wayne can become a best-selling rapper, than ANYTHING is possible.  The guy has the vocabulary of a six-year old and his voice sounds like a combination of Fran Dresser and Alvin the Chipmunk. MTV listed Lil Wayne as number two on their hottest MC’s of 2009.  Are you fucking kidding me? If you want to hear good rap music see: Tupac, Notorious B.I.G or Big L. Unfortunately they are all dead. Why do only the good rappers get shot? Lil Wayne says he’ll be writing and rapping during his stay on Riker’s Island, so we have all his new “music” to look forward to in about 8 months to a year.  Edit: This was written before he got sentenced to a year in jail.

Hank and Hal Steinbrenner

Talk about winning the DNA lottery! These two have inherited the most successful franchise in all of professional sports from their daddy George Steinbrenner. The boss handed his sons the reigns to the 27-time champion Yankees in late 2007. What makes this story even more remarkable is that these two weren’t even in line to take over the Yankees originally. Steinbrenner’s then-Son-in-Law, Steve Swindal was in line to take over the team. However a DUI arrest in 2007 started a chain of events that led to his divorce from Jenny Steinbrenner and eventual exile from the Yankees Empire, thus leading the way for Hal and Hank to take over the team.

Levi Johnston

A few years ago, Levi Johnston was just some douchebag in Alaska who knocked up an unknown governor’s daughter. Then Sarah Palin was thrust into the vice-presidential race and Johnston’s face was plastered all over Fox News. Now the Father of the Year has ditched his baby mama and is doing Playgirl spreads and starring in Pistachio commercials. The moral of this story folks: If have unprotected sex with a politicians’ daughter, knock her up and then abandon her, then you too can be rich and famous.

Mike “The Situation” Sorrentino

I could really talk about any of the cast members of Jersey Shore but “The Situation” stands above the rest. His face looks like an old catcher’s mitt but he has nice abs and a fake tan, (and now has money) so there are probably an abundance of trashy women willing to sleep with him. He’s done nothing to achieve his fame and fortune other than making an ass of himself and coming up with a catchy name for his midsection.

Dane Cook

Dane Cook has yet to tell a joke that has made us laugh, yet he’s doing shows all over the world and selling out Madison Square Garden. So how does he do it? The answer is simple: teenage girls. Every 14-year old girl in America LOVES this guy. I’m not quite sure why, but they do. You CANNOT underestimate the buying power of teenage girls. Just look at all the money Harry Potter and Twilight made. Maybe Dane Cook is a genius. Perhaps he knew all along that he should gear his comedy toward pre-pubescent women. DAMN. Well played, Dane Cook. Well played.

John runs a site called Living with Balls.  He can also be found on Twitter.

Around The Web

  • RalOberon
    March 11, 2010


    I could actually add a few. For instance, why has KFed not made the cut?

  • Living with Balls
    March 11, 2010


    You’re right. K- Fed is a good one. Damn I could have written some good stuff about him.

  • Magpie
    March 12, 2010


    Ha, I liked this… Dane Cook is a douche and I don’t even know who that Mike guy is but anyone who names their anatomy is painful to watch.. Ugh.

  • sleeping bags
    March 15, 2010


    Levi Johnston,

  • Mike
    March 15, 2010


    I don’t care WHAT anyone says. Every man on this planet would want to be Ron Jeremy! Thousand pornos, thousands upon thousands of women, and he is not only still alive (think every other porn star from his era), but HE’S STILL WORKING!!!!! He’s got to be put in the Guiness Book of World Records!

    No gold watch on earth could commerate his achievements!

  • peter
    March 15, 2010


    simon cowell???? hugh grant? jude law? yes, most british guys have no talent, but an annoying charm that women love

  • sonni
    March 15, 2010


    What about Jay-Z?

    • j
      March 28, 2010


      no, hardest working man in the biz.

  • madtown
    March 15, 2010


    I think tucker max should be among these losers

  • Beelzebub
    March 16, 2010


    I agree with all said except Seal, He has TWO hit songs and his disorder is only on his face. He and his wife have 3 kids.

  • John
    March 17, 2010


    none of the people on the list could have a star on the hollywood walk of fame. Maybe Weezie shouldn’t have made this list, because at least he take care of his baby mammies, lol

  • Living with Balls
    March 18, 2010


    Tucker Max is an asshole but his book his hilarious and well written. I don’t think he should make the cut.

    Jay-Z is one of the best rappers of all-time.

  • Greg
    March 28, 2010


    Seal shouldn’t be on the list. He’s had many successful songs and is way more fucking talented than most ‘artists’ today, including the prick that created this post. He’s actually very attractive, even with the scars. Again, probably more so than the fat slob that made this post.

  • Living with Balls
    March 30, 2010


    FYI Greg. I wrote this post and I am neither fat or a slob. Nothing I write should ever be taken seriously. So take it easy.

  • Jester of the Apocalypse
    April 3, 2010


    Everyone knows the luckiest man in the world is . . . THE DRUMMER FOR ZZ TOP!!!

  • crystal
    May 15, 2010


    Tony Danza. Just…no.

  • muttaka
    July 16, 2010


    My luckiest man in america is lilwayne

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