From Dr. Dre To Sir Mix-A-Lot: Hip-Hop’s Greatest Road Trip Songs

From Dr. Dre To Sir Mix-A-Lot: Hip-Hop’s Greatest Road Trip Songs

The global coronavirus pandemic has led to so many having to spend hours upon hours stuck inside. The effect of widespread quarantining means many are feeling stifled and sequestered in their homes. And it's so unfortunate, because the road can be therapeutic. Cruising can hold a unique spiritual freedom; getting behind the wheel can be as close as many of us get to "getting away from it all." The only thing better than hopping in the car and riding to nowhere is having a great soundtrack to push things along. Songs about the open road are a great American tradition – from “Rocket 88” to “Freeway of Love.” In Hip-Hop, those songs convey a sense of freedom and identity, beyond just the allure of hitting the highway, there’s also the sense of self that comes from riding around the neighborhood, speakers blaring, rims spinning. Whether long drives, or slowly rollin' the streets on a Sunday—these are some classic rap road songs that you'd have on deck.

For the Riders: All-Purpose Anthems

“My Hooptie” – Sir Mix-A-Lot (1989)

As Hip-Hop became more obsessed with flashy, luxury vehicles, it’s sometimes great to think back to when it was cool to rap about the kind of junker we all had to push at some point or another.

There’s no better ode to the lemon than Mix-A-Lot’s classic “My Hooptie,” featuring an always broken windshield, non-working meters   and dragging tailpipe. Sir Mix-A-Lot had a knack for story raps about cruising with his boys, and while “Posse On Broadway” might be more beloved, “My Hooptie” is the quintessential everyman car song. We’ve all had this car.

“24s” – T.I. (2003)

Tip has a few songs that define the early 2000s, and “Top Back” is another car banger that could have easily been on this list. But it was this ode to bigass rims that helped set things off for Clifford Harris’ early career, and the hook is one of his best. 

Produced by DJ Toomp, it perfectly captures ATL swagger and the car culture that defines so much of southern rap from Miami to Atlanta to Houston. And T.I. is on one throughout the track. “I'm in a drop-top Chevy with the roof wide open/My partners looking at me to see if my eyes open/Cause I've been dranking and I've been smoking…” A ridin’ masterpiece.

Ridin' - Chamillionaire feat. Krayzie Bone (2005)

“Ridin’” – Chamillionaire feat. Krayzie Bone (2006)

The thrill of driving is as American as apple pie — but the reality of “Driving While Black” is just as inherent in the experience of so many young Black people. This classic hit from Chamillionaire illustrates the duality of both:  it’s an undeniable car classic that also functions as a harrowing tale of how just being a brotha cruising in your ride can lead to an altercation with the cops.

The Texas rapper was inspired by UGK’s classic 1996 album, and with a heavy assist from Krayzie, Cham makes it clear that, for certain folks, there is no easy liberation to be found in going for a ride in the whip. But he also couches that message in a song that functions as perfect car music. Quite a trick to pull off.

Block Bangers for Urban Road Warriors

“You’re Gonna Get Yours” – Public Enemy (1987)

P.E.’s first album is bombastic and aggressive, but it may surprise younger listeners with how it’s not quite as focused on righteous, raging rhetoric as their later, more famous works. 

The clearest example of Chuck D’s early approach is this car-themed classic. Often casually referred to as “My ’98 Oldsmobile” it features Chuck rhyming over an almost Run-DMC-esque truck rattling beat courtesy of the Bomb Squad, where he makes his Olds sound like an urban terrain vehicle made for b-boys. He rhymes about his ride as if it’s his only protection against the suckas hatin.’ Tell me you can’t relate. Perfect anthem for any road warrior.

 “The Boomin’ System” – LL COOL J (1990)

LL was blanking out throughout Mama Said Knock You Out, a classic album with no shortage of bangers. But this car anthem classic made it clear that James Todd Smith knew a thing or three about having a dope-ass system in your car. A sentiment that resonated with heads from Queens to Cali, LL perfectly tapped into the energy of riding around with the system loud as hell.

“Let’s Ride” – Q-Tip (1999)

The former A Tribe Called Quest frontman’s solo debut Amplified may be most remembered for shiny pop singles like “Breathe & Stop” and the ubiquitous “Vivrant Thing,” but it was this chill ode to riding in your whip that best crystalizes who Kamal Fareed was going to be circa Y2K. 

Name-dropping the classic rock of The Who alongside the Hip-Hop du jour of Biggie, Q-Tip makes a perfect case for rolling to the sounds of your choice and not letting the outside world interrupt the groove.

Impala Anthems: For Sittin’ Sideways On a Southern Slab

“Drive Slow” – Kanye West feat. Paul Wall (2005)

‘Ye was in full bloom on Late Registration, and this Paul Wall-assisted, southern-flavored tribute to riding was one of the standouts on an album that many still consider Yeezy’s best. Over an inspired Hank Crawford sample, ‘Ye and Wall rap about car culture as a metaphor for life, and Wall almost missed the session. 

“I got pulled over on the way to the studio,“ he said in 2016. "My driver made a right turn from the wrong lane. “I said, ‘Hell nah. This ain’t real.’ I cussed the police out thinking I was getting ‘Punk’d. I almost ain’t make it.”

The remix featured a verse from T.I. and the video is an orgy of dope cars. “That verse was actually the first verse that I wrote when I was writing ‘Sittin’ Sidewayz,'” explained Paul. “Back in those days, I didn’t know how to harness the power of the production sometimes.” In the end, he decided that those rhymes were “hard” but, “Didn’t really go hand-in-hand with that beat.”

“Lacville ’79” – Devin The Dude (2002)

Devin is Hip-Hop’s most laconic storyteller; like a laid-back cousin who tells stories better than anybody else in the family. His classic single breaks down the joys of having a car that’s all your own — warts and all. 

Like Mix-A-Lot’s “My Hooptie,” this is an ode to a car that we all have owned at some point, and it’s the perfect anthem for hitting the road on a lazy afternoon or two. It also wouldn’t hurt to have a doobie in the ashtray — not that anyone’s advocating that sort of thing.

“Still Tippin’” – Mike Jones feat. Paul Wall and Slim Thug (2004)

It’s slow as syrup and perfectly encapsulates Houston’s car culture in a genre-defining four and a half minutes. Mike Jones never quite topped his debut single, a tribute to chopped-and-screwed sound of DJ Screw and to a uniquely Texas flavor of rap that had been a part of southern rap since the early 1990s. 

The whole song is a dedication to cruising, and of course "tippin' on four 4s, wrapped in four Vogues." It dropped the Houston sound smack dab into the middle of the mainstream, made stars out of Paul Wall and Slim Thug — and ensured that no one would have to ask “Who is Mike Jones?” ever again.


 Lowrider Leaning: Classics for Cali Cruisin’...

“Let Me Ride” – Dr. Dre (1993)

The good Doctor’s G-Funk classic perfectly captures the essence of The Chronic and the feel of So Cal cruising. Even if you’ve never seen Crenshaw and Slauson, the slice of laid-back Cali cool puts you right there. The gunplay and tough talk are there, but take a backseat to the feel good vibe of rollin’ in ya 64, a sentiment that anyone can relate to who has ever gone for a Sunday road trip on a gorgeous day.

“High Til I Die” – 2Pac (1996)

This song isn’t exactly about a car or about driving, but it perfectly captures a certain feel associated with carefree cruising when you got nowhere to go. Like a lot of Pac anthems, the freewheeling feel belies lyrics that warn of danger at every turn — even while sounding unaffected (“When I'm in traffic, it's kinda rough and, I drive a bucket, Live the Thug Life nigga – screaming ‘fuck it’”). It’s quintessential Pac, and a perfect thug anthem for a ride.

 “Jeep Ass Niguh/Born To Roll” – Masta Ace (1993, 1994)

Former Juice Crewer and Brooklyn legend Masta Ace became a somewhat unlikely advocate for Hip-Hop car culture in the mid-1990s. The rhyme animal semi-reinvented himself as a cruise anthem rapper with hits like this. Of course, “Jeep Ass Niguh” first appeared in 1993s Slaughterhouse before it was reinvented as the decidedly West Coast-leaning “Born To Roll” a year later. It gave Ace one of his biggest crossover hits and came to define car songs that Cali loved in the 1990s. He would dive headfirst into the sound on 1995s Sittin’ On Chrome, but this was his first foray into such subject matter — and still his best.

* HEADER CREDIT: Dr. Dre and Fab 5 Freddy during 1993 MTV Video Music Awards at Universal Amphitheater in Los Angeles, California. (Photo by Jeff Kravitz/FilmMagic, Inc)

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