The Top 10 Presidents More Gangsta Than Obama

March 24, 2009

John F. Kennedy was the David Bowie of U.S. Presidents – he made the hallowed office a glam position, and the current Commander in Chief is no different.  But they're not even close to being the best we've ever had.

Source: Dmitry Astakhov/Getty Images

10. Ulysses S. Grant


Source: National Archives/Getty Images

Grant was a major, major drunk.  He won the Civil War for the Union effectively uniting these United States, but he definitely did it completely sloshed.  He was also one of the best overall military commanders in this country's history.  But, shoot, that don’t mean he didn't like to party, son. His love for battle-side bottle service is totally documented, and he still kept his (and the country’s) affairs in perfect order.  Barack, on the other hand, cannot party for f*** all.

Contemporary Gangsta Equivalent: J-Kwon

9. Dwight D. Eisenhower


Source: Gene Forte/Hulton Archive/Getty Images

Eisenhower was a baller, dude. He initially wanted to be a professional baseball player, but he also had crazy skills on the gridiron.  He didn’t make the baseball team at West Point, but did start as a varsity running back and linebacker.  And this was in 1912 before football was pussified with pads and cortisone shots.  He even took down Jim Thorpe and scored such a spectacular touchdown that it was reported on in the New York Herald.  Also, he was the most powerful man in the world, a  general, and he made Hawaii a state, paving the way for sweet, thonged honies running on American beaches.

Barack, on the other hand, is pretty good at golf.

Contemporary Gangsta Equivalent: Nelly

8. Harry S. Truman


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Harry Truman didn’t have a middle name.  The S. was just an S., but I submit here that henceforth it stands for "Sucka-free" because this motherf**** was in office to do two things: drop bombs and stop bucks.  And, to be honest, they ran out of bucks pretty quickly.  That’s not to say Truman was low on scrilla.  The dude got $670,000 to write his memoirs after he left office.  Oh, also, this guy tried to kill him, but just ended up getting lit up like a Christmas tree by Truman’s crew (a.k.a. the Secret Service).

It’s like House of Pain said: Words to your moms, I came to drop bombs, I've got more rhymes than the bible's got psalms.

Contemporary Gangsta Equivalent: House of Pain

7. Rutherford B. Hayes


Source: Matthew Brady

“What up Rutherford B. Hayes?  Oh, just getting shot at?  Cool, cool.”  That’s what pretty much all of Rutherford’s friends would say to him.  He served in the Civil War, like a few other Presidents, but unlike those presidents he was wounded in battle four G.D. times.  However, he could not be killed with conventional weapons.  He also had four horses (who can be killed by conventional weapons) shot out from under him.  After that, he decided it was time to be President which, by comparison, was pretty boring.  So he focused mostly on just keepin’ it real with his crew by passing the Timber and Stone Act, likely in order to finance bitchin’ pool parties.

Obama has been shot zero times in all of his zero battles.  Fact.

Contemporary Gangsta Equivalent: 50 Cent

6. Teddy Roosevelt



Teddy Roosevelt basically did not f*** around when it came to straight keepin’ fools in check.  In 1898, when he was the Assistant Secretary of the Navy, Teddy Roosevelt was jockeying for war with Spain.  As part of his play to fight Spaniards, he organized and lead the 1st U.S. Volunteer Cavalry Regiment, more popularly known as the Rough Riders.  This guy, the future President of the United States, just got a bunch of his buddies together, got some horses, and road those mothas into Cuba to kill some people in a war he started.  He also studied judo and had his face carved into a giant mountain.

Obama can sketch.

Contemporary Gangsta Equivalent: DMX

5. George Washington


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George Washington founded the greatest nation on Earth.  That’s pretty rad – it takes a lot of hustlin’ to set up a country, especially one like this country.  However, the reason General Washington makes this list is because he had the world’s first grill.  Dude rocked that s***.  And, guess what, they weren’t wooden.  Nope.  That’s an urban legend.  Big George’s bling was made of “the finest hippopotamus ivory and gold.”

Daaaaaaamn. Obama won’t even buy his wife proper bling.

Contemporary Gangsta Equivalent: Paul Wall   

4. Thomas Jefferson


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T.J. was a straight pimp through and through.  Sure he had a first lady.  He also had a second, third, fourth and fifth lady.  And, I tell you what, T.J. liked the thicker girls.  Some historians claim that he had a harem of slaves, but there is little-to-no evidence proving that they didn’t love the lovin’ they were gettin’. Another thing about Jefferson is that he just really hated banks.  He wanted nothing to do with them, so his accumulated wealth (which was substantial) was all in liquefiable things like, say, pimp cups.

Contemporary Gangsta Equivalent: Jay-Z

3. Andrew Jackson


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This man fought 13 pistol duels in his lifetime. He only killed one of the men – duels often didn’t result in death because participants, out of honor, purposefully missed.  Even if you did aim at your opponent, though, the pistols were pretty inaccurate. So what pissed off President Jackson so much that he actually shot and killed a man? Charles Dickenson owed him money on a horse racing debt.

Jackson also spent his entire adult life with a debilitating case of dysentery because he spent most of his young life in swamps hunting the most dangerous game:  Native Americans.

Contemporary Gangsta Equivalent: C-Murder

2. Jefferson Davis – reppin’ the East Coast South


Source: Netterville Briggs/Hulton Archive/Getty Images

As President of the Confederate South, Jefferson Davis had an uphill battle from the get-go. Even after General Lee surrendered to Ulysses S. Grant in 1865, Jefferson Davis and his administration urged the South to keep on fighting.  In fact, they went on a door-to-door campaign throughout the South trying to get a guerrilla army to rise up and defeat the North.  Even after not a single family in the entire South would let them stay on their land, this plucky Prez still refused to surrender. He was thrown in jail for two years after being tried for high treason.

Barrack was raised by a single mom in a tropical paradise.  That’s tough. 

Contemporary Gangsta Equivalent: Biggie

1. Abraham Lincoln


Source: National Archive

Lincoln ended slavery and maintained the union during the Civil War.  Without him we’d just be the Slave-y States of America, and that’s no good at all. He also gave man-birth to an entire type of debate (Lincoln-Douglas) because he could spit rhyme so fast and furiously.  He also did this while he contracted frostbite, malaria, smallpox, and syphilis.  He probably had a lot of those from bangin’ honeys on the side because, because his old lady was kind of a b****.

Anyway, being unapologetic and brazen like a true gangsta, Lincoln became the first President to be assassinated in, as we all recall, the Ultimate Showdown of Ultimate Destiny.

Contemporary Gangsta Equivalent: Tupac