I’d jump at the chance to be any of these guys rather than myself.
10. Robert De Niro as Jimmy “The Gent” Conway in Goodfellas 1990. This character was based on the real life Irish-American gangster and Lucchese crime family associate James Burke. (Try to test my mob knowledge, I dare you.) It’s been said he was involved in over 50 murders. James Burke was kind of an asshole. After the famous Lufthansa heist he murdered everyone in on the job so he wouldn’t have to share the reported five million dollars. This is well documented in the movie Goodfellas. The fictional character Jimmy Conway had a little more swagger about him. Three reasons to be Jimmy Conway: 1. Wear expensive suits every day. 2. Never pay for another drink, ever. 3. Anyone with a brain fears you.
9. Jeff Bridges as Jeff “The Dude” Lebowski in The Big Lebowski 1998. This character was based on the real life person Jeff Dowd, a political activist and member of the “Seattle Seven” (radical anti-Vietnam War movement.) The Dude is a single, unemployed slacker living in Venice Beach, California who only loves three things (other than pussy): White Russians, weed, and bowling. Who doesn’t want to be this man?! Three reasons to be Lebowski: 1. Only wear clothes that give new meaning to the word comfortable. 2. Give a fuck about nothing. 3. Your best friend is this guy:
Walter doesn’t “fucking roll!” on Shomer Shabbos neither. I thought of a 4th reason being The Dude would kill: using roach clips in the tub while taking a stoner bath surrounded by candles. This dude knows how to live!
8. Ewan McGregor as Mark “Rent Boy” Renton in Trainspotting 1996. Renton chooses not to choose life and instead picks a good old-fashioned heroin habit. Remember the girl Diane he met at the dance club and then hopped in the taxi with after? Granted, she was fifteen years old, but he gave her the good old fashioned in & out before knowing that. She was pretty much slammin’ hot. Heroin and you get to fuck a 15-year-old?
Please. Three reasons to be Renton: 1. One of your best friends is named “Sick Boy.” 2. Have no fear of shitting in public restrooms. 3. One day sober up and start writing because if history has taught us anything it’s that ex-heroin addicts make for amazing authors. What can you possibly know about life until you’ve almost pissed yours away?
7. Don Cheadle as “Rocket” in Colors 1988. Rocket was the leader of the Crips gang in Los Angeles, California. A poor street gangster with no future or value of life equals a ruthless murdering psychopath. Rocket loved one thing and one thing only: killing Bloods. This dude was the illest character I’d ever seen at 10 years old. I wanted to be him and this movie being responsible for my life-long obsessed with street gang culture. Three reasons to be Rocket: 1. Kill people with Uzi machine guns. 2. Wear bandanas on your head. 3. Die in a hail of bullets and in the process be forever immortalized as a gang legend.
6. Jason Lee as “Brodie Bruce” in Mallrats 1995. This guy kills. Everything out of his mouth can be documented as a memorable quote. Similar to The Dude in The Big Lebowski, Brodie is an unemployed, comic-book-obsessed, Sega-playing slacker who lives with his parents and refuses to grow up. The mall is his life. The dude has so much self-confidence he could practically fuck anyone and it’s this same arrogance that leads to him hosting his own late-night talk show. Plus I’m pretty sure Shannen Doherty would be amazing to have sex with. Three reasons to be Brodie: 1. Host your own late night talk show. 2. Fuck Shannen Doherty. 3. Two of your best friends (Jay and Silent Bob) are willing to fulfill any request at a moment’s notice. This is illustrated in the film when Brodie asks them to destroy a talk-show stage. (They fail, but it’s the thought that counts.)
5. Daniel Day-Lewis as Bill “The Butcher” Cutting in Gangs of New York 2002. This character was based on a real-life person named William Poole (1821-1855). In the film Bill dies at the hands of Leonardo DiCaprio’s blade, but the real William Poole died from a gunshot wound in a bar. He actually died later at home with his wife and children. His last words were, “Good-bye boys, I die a true American.” Dude was for real. At one point in the film Bill tells the story of why he has one glass eye. The Priest (Leo’s father) once beat the living hell out of Bill. The Butcher was too ashamed of himself to look the Priest in the eye when it came time to die, so instead of killing him, the Priest let Bill live in shame. The Butcher then walked home in humiliation, cut his own eye out, and sent it to the Priest as a message he wasn’t ashamed anymore. Bill then rose up again with a full heart and buried the Priest. Dude stuff—fucking awesome. Three reasons to be Bill: 1. Your nickname is “The Butcher.” 2. Draping yourself in the American flag after being shot in a failed assassination attempt. 3. Kill people with meat cleavers.
4. Christian Slater as “Brian Kelly” in Gleaming the Cube 1989. Brian was a punk skateboarder who starts investigating his adopted Vietnamese brother’s strange death. He ends up solving the crime and puts his life back together in the process. Plus I always got the vibe he totally banged his dead brother’s girlfriend. If you’ve ever wondered what a 9-year0old boy considers the most amazing situation that could ever unfold, it’s bombing a hill on your skateboard to escape Vietnamese gangsters on motorcycles. Are you kidding me?! I still think that’s cool. Three reasons to be Brian: 1. The Bones Brigade are your best friends. 2. You vent the frustrations of chicks & shit by shredding a half-pipe. 3. You know a gullible airline pilot who takes you up in his Cessna airplane in search for empty pools to skate.
3. Ryan Phillippe as “Sebastian Valmont” in Cruel Intentions 1999. All this dude cared about is pussy. He later falls in love for the first time with Reese Witherspoon’s character and dies while saving her life, but before that his days were spent manipulating dull beautiful girls into becoming his sex slaves. Say what you will, but this is a gangster-ass film and should be a part of your movie collection. One chick is a coked-out whore who convinces Sebastian to buttfuck a girl she was dumped over. The girl in question was secretly fucking her black music instructor and one enraged therapist, angry over the fact Sebastian fucked her daughter and then put it on the Internet. The script is based on a book written by Pierre Choderlos de Laclos titled Les Liaisons Dangereuses in the year 1782. The original story centers around two ex-lovers who use sex as a weapon to humiliate and degrade others, all while enjoying their cruel game. Hence the title, Cruel Intentions. See, you learn something new everyday! Three reasons to be Sebastian: 1. You get to be young, rich, and live in New York. 2. You drive a convertible vintage Jaguar. 3. No woman is out of your league.
2. Matthew Broderick as “Ferris Bueller” in Ferris Bueller’s Day Off 1986. Come on, you knew this was coming. John Hughes is godlike when it comes to screenwriting and it was very difficult to only choose one character here. Honorable mention: Judd Nelson in The Breakfast Club. Ferris had a lot more wit than Bender and used it to get out of school for a day of adventuring. This film only cost 5 million dollars to make and grossed over 70. That’s a successful script when it brings in 65 million dollars in profit. It’s not hard to convince a movie studio to finance your screenplay when you have a reputation for earning that much money. Remember when Ferris ended up on the float in a parade singing “Danke Schoen” and “Twist and Shout”? He’s wearing that leopard vest over a white T-shirt, blue slacks, and white shoes. His girlfriend’s panties are so wet if she took them off and then threw them against a wall, they would stick.
Who didn’t want to be this dude? Three reasons to be Ferris Bueller: 1. Your sister is Jennifer Grey and if you’re crazy enough you can try to fuck her (Ferris could somehow pull this off and it wouldn’t be creepy.) 2. You make out with chicks in art museums. 3. Your best friend is clearly a psychopath who will one day snap and murder 80 people (you get to be on the news as his best friend to tell the story.)
1. Jack Nicholson as “Jack Napier/The Joker” in Batman 1989. Jack Napier was born in Brooklyn and later moved to Gotham. While attending school he proved to be emotionally unstable but highly intelligent, showing aptitude in art, science, and chemistry. He also turned to a life of violent crimes. As a young man he murdered Batman’s parents. He rose to the top of organized crime in Gotham City by becoming the right-hand man to the big boss Carl Grissom. He even started fucking Grissom’s wife. Jack Napier was a gangster through & through and was believed to be killed after being dropped by Batman into a vat of toxic waste. But he didn’t die. He was washed into the Gotham Harbor by a drainage pipe. The waste had a negative effect on Jack’s body. His hair follicles were altered so they grew hair emerald green, his skin pigmentation was bleached chalk-white, and the soft flesh of his mouth and lips were flushed ruby red. Jack’s mindset completely snapped and the Joker was born. He used weapons such as bladed playing cards, an acid-squirting flower, cyanide-stuffed pies, exploding cigars filled with nitroglycerin, harpoon guns, and a lethally electric joy buzzer. His favorite was his “Joker venom,” a deadly poison that infects his victims with a ghoulish grin as they die laughing hysterically. The Joker is the greatest supervillain of all time. And fuck Heath Ledger—Jack Nicholson was the real Joker. Heath Ledger was a twat. The dude had a three-year-old daughter and overdosed on like six different drugs? What an asshole. Three reasons to be gangster-ass Jack for three decades and then go out with a bang as the Joker: 1. Look great in pictures. 2. Destroy something beautiful (pour acid on supermodel’s face). 3. Be psycho.