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A Hip-Hop Fan's Ode to Cadillacs

OutKast, Ludacris and more introduced me to the Cadillac, my dream car.
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My young, adolescent eyes didn’t know the first sight of love until the day they saw her sitting in my neighbor's driveway. Underneath the unforgiving summer sun, she was the shining definition of what my world was missing. Every boy has a moment in his life when he first lays eyes on his dream car—art in the form of a vehicle—and what I saw was a machine more beautiful than the Mona Lisa: a 1973 Cadillac de Ville sedan.

The car was marble white with a long frame, like a spaceship on wheels. It was more elegant than a galloping Seabiscuit, sophisticated as the Taj Mahal, and too expensive for a boy who needed diamonds and gold but was working the graveyard shift for pennies and dimes. Before my neighbor sold the car, I sat behind the wheel once, and as I sunk into the cushy seats and gripped the steering wheel, I couldn’t help but think of all the rap songs that inspired my appreciation for classic Caddies.

Big Boi and André, the pimp and the poet, and the greatest rap duo to ever come from Atlanta’s red clay, are who I give credit to for making Caddies synonymous with the South. To be a fan of Kast is to appreciate the one-of-a-kind car that was mentioned most often throughout their outstanding career. If there were a third member in OutKast, it would be an old school Cadillac. It’s in the title of their debut album, Southernplayalisticadillacmuzik. Their sophomore classic, ATLiens, is home to the timeless “Two Dope Boyz (In A Cadillac).” It’s a song that makes you want to drive topless in a Caddy with your best friend, burning rubber down an empty highway, whistling at beautiful women while the song plays loud enough to be heard in heaven. They made Caddy’s seem luxurious, but not exclusive, more like the birthright for any boy growing up in the Southern states. You have drawl, your collard greens, and your Cadillacs―the Southern trinity.

“Diamond In The Back” by Ludacris encapsulated my Cadillac dreams. He was rapping from the perspective of a young boy who had very little but dreamed of diamond-backed, sunroof-topped Cadillacs, referring to the old school 1970-80 models. They were the cars that all the pimps, players, and drug dealers were driving. Luda captures the natural allure of materialistic toys from the eyes of an innocent boy who just wants to drive in the cleanest whips, and who is racking his brain on the quickest way to get there. It’s such a simple wish, but the smallest things to adults tend to be the biggest to a child. “Diamond In The Back” framed the Cadillac as a car of fantasy, one that you had to have by any means necessary. It’s funny, the song he samples is William De Vaughn's “Be Thankful For What You Got.”

Rich Boy brought Cadillacs and rim culture back to the forefront of the mainstream when "Throw Some D’s" dropped in 2006. Pimp My Ride was already popular, the spinning rims were already popular, but Rich Boy brought together both in a popular song. Rich Boy was like a little boy in “Diamond In The Back,” except he sold a little crack and got the Caddy he always wanted. The music video was like a parade of all the cars after they leave Xzibit’s garage. Rich Boy’s “Throw Some D’s” and Dorrough’s “Ice Cream Paint Job” were some of the last big car hits that took over both radio and clubs. Rap moves in phases, the car phase was a big one, and I’m certain it caused both old and new Cadillacs to sell. It was a good time to be in the South; I can recall all the car clubs bringing their whips out, and being in awe of the paint, the rims and all the minor and major customization.



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Cadillacs and pimps go together like Jack and Coke, Meek Mill and Rollies, Cash Money and lawsuits; they are a match made in Eden before any apple was bitten. When I think about pimps and Caddies, the first song that comes to mind is Do Or Die’s “Po Pimp.” The ‘96 Chicago classic captures the essence of cool. From the debonair hook to the most suave of verses. If someone asked me what pimping sounded like, this would be one of the first songs to come to mind. You can imagine the stylish suits, the expensive furs, the exorbitant canes and the gorgeous women inside the most gaudy of Cadillacs. OutKast may have “Player's Ball,” but “Po Pimp” would be the soundtrack for Silky Johnson, Buck Nasty, Mr. Roboto and Ice-T. Do Or Die didn’t just give us audio pimping, but a Twista feature that introduced many to the super faster spitter. As long as there are Cadillacs on the road, as long as there women cozy in the backseats, “Po Pimp” will be blasting from the speakers, and the world is better for it.

A lot of newer rappers are into foreign cars, but it seems more like a stunt than a vehicle they actually care to drive. When I listen to Big K.R.I.T., the way he talks about Cadillacs, you can tell he’s a true lover of the car and the brand. He’s also a Southern born and raised rapper. I’m pretty sure growing up on David Banner, Ludacris, and OutKast played a significant role in his immense appreciation for the cars. Krizzle can be the pimp, the playa and the poet who cares about his subs, paint job and rims. If there’s any artist who will make the next generation of rap fans really admire Caddies, it’s going to be K.R.I.T. Just like OutKast, he put the car in the title of his album Cadillactica. I have such immense respect for how he carries Southern traditions in his music. K.R.I.T has never run from his Southern roots, but embraces them and continues to be a beacon of life for Southern hip-hop. If you have a Cadillac and you are not playing K.R.I.T., you are wasting perfectly good speakers.

UGK, Daz Dillinger, Snoop Dogg, Devin The Dude, Master P, Freddie Gibbs; the list of rappers who have paid homage and dedicated odes to the highly favored vehicles goes on and on. Some items are just forever connected and desired because of hip-hop. Jay Z made people want to buy Cristal, Kanye made people want Louis Vuitton, but what hip-hop made me want most was a Cadillac. Hopefully, after my first best seller, I’ll be able to buy that 1973 Cadillac de Ville, and drive down the highway bumping a playlist of all those acknowledged in this article.

A man can dream, right?

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By Yoh, aka Two Dope Yohz (In A Cadillac), aka @Yoh31.



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