The Great Rides of Song

America is a nation on the move. From horse-drawn wagons to steam locomotives to the internal-combustion engine of today, transportation has kept these states united on the freeway to tomorrow. To the factory and office, the church and school, the dope spot and drive-by, and back home again — there’s nothing like the perfect luxury automobile to get you there in style. Whether it’s a Benzo, Lexus, or ragtop Caddy, the right car lets show your status, find a word that rhymes with “Texas,” and tell a rags-to-riches tale in just one Chevy-to-Bentley couplet. So join us as we cruise through thirty years of innovation — from Old-School American sedan to Southern-bounce Japanese import – in this brief rap history of automotive design.

1979-present: Lincoln Continental

Powered by Ford’s massive 460 V8, this highly equipped luxury car was surpassed in size only by Cadillac’s Fleetwood 75 limousine. Fly boys and playas overlook the 10-mpg fuel efficiency in favor of its non-wack style, expansive girly-accomodating cabin, and reasonable day rate.

“I got two big cars that definitely ain’t the wack/I got a Lincoln Continental and a sunroof Cadillac.” — Sugar Hill Gang, “Rapper’s Delight,” 1979.
“Went to the prom, wore the fly blue rental/Got six girlies in my Lincoln Continental.” — Beastie Boys, “The New Style,” 1986.
“I’ll be gentle, sentimental/Shit, we fucked in a rental/Lincoln Continental.” — Snoop Dogg, “Bitch Please,” 1999.

1983–present: Cadillac (Brougham, DeVille, Fleetwood, Seville)

The jewel in the crown of General Motors, the Cadillac brand symbolized wealth and prosperity in America’s postwar years, gas-guzzling excess in the late-’70s, and pimp-ass player shit throughout some 30 years of rap. This last reputation first began in the 1930s, after Joe Louis was barred from a dealership due to his race. In response, Cadillac executive president Nicholas Dreystadt aimed new advertising directly at black consumers, and since the late ’70s, American raps have consistently provided brand endorsements and the kind of customer consultation that produced the mink-lined, three-TV-screen-appointed Snoop DeVille.

“I got a big long Caddy, not like a Seville/And written right on the side it reads ‘Dressed To Kill.” — Run/DMC, “It’s Like That/Sucker MCs,” 1983.
“I’m about to fuck up the program/Shooting out the windows of a drop-top Brougham.” — Ice Cube, “The Nigga Ya Love To Hate,” 1980.
“It goes chromes to the Fleetwoods, coupes to the ‘Villes/Hittin’ Girbauds and off these flows we havin’ the playa chill.” –Outkast, “Two Dope Boyz (In A Cadillac),” 1996.

1988-present: Mercedes-Benz

Seventeen years after its lyrical debut in a Janis Joplin song, this German luxury-auto company was celebrated in a noted single by a Los Angeles quintet expressing reservations about their local law enforcement. As wealth replaced protest as hip-hop’s central trope, the Mercedes-Benz became the all-but-official Car of Rap, the most consistently referenced vehicle brand of the last 20 years.

“You’d rather see me in the pen/Than me and Lorenzo/Rollin’ in a Benzo.” — N.W.A., Fuck Tha Police,” 1988.
“Picture me rollin’ in my 500 Benz/I got no love for these niggaz, there’s no need to be friends.” — 2Pac, “Picture Me Rollin’,” 1996.
“If I went back to a hooptie from a Benz/Would you poof and disappear like some of my friends.” — 50 Cent, “21 Questions,” 2003.

1990-1998: Mustang 5.0 L

It was Ford’s leading sports-class automobile since its 1964 introduction at the New York World’s Fair. The pioneering “pony car” received a third-generation redesign that gave it a roomier backseat and a more aerodynamic body, and the 5.0 (actually a 4.9 liter/302 cid) came to inspire one of the largest aftermarket industries in the United States. Already boxier car than the sleek 390 cid Fastback that costarred with Steve McQueen in the 1968 film Bullitt, the early-‘90s Mustang underwent the most drastic coolness downgrade in automotive history, thanks to a Caucasian rapper born Rob Van Winkle who boasted of a “flow like a harpoon.”

“Rollin’ in my 5.0/With my ragtop down so my hair can blow.” — Vanilla Ice, “Ice Ice Baby.” 1990.

1992-present: Chevy Impala

The most expensive marque in the Chevrolet line-up, the second-generation Impala was produced on a rear-wheel-drive GM B platform with rounded exterior styling and made available with either a small-block 327 cid engine or the big-block option referenced in the Beach Boys’ song “409.” Thirty years later, another West Coast retrofit added multiple hydraulic pumps, galactic woofers, recessed Glocks, and rack-and-pinion dizzank to create the preferred creepin’ conveyance of Compton and Long Beach g’s, ho’s, and other discriminating motorists.

“Rollin’ in my Fo’ with the switches/And got sounds for the bitches, clockin’ all the riches.” — Dr. Dre, “Let Me Ride,” 1992.
“Wanna be a baller, shot-caller/Twenty-inch blades on the Impala.” — Lil’ Troy, “Wanna Be A Baller,” 1999.

1993-present: Jeep

With a proud history of American military service dating back to World War II, this oldest of off-road vehicles was first produced as a civilian model in 1945 by the Willys- Overland company, then purchased by Kaiser, then AMC, before Chrysler secured the copyright in 1987. Since then, its standard design has featured a distinctive seven-slot grill, four-wheel drive, solid front and rear axles and backseats with full episode-swinging capability—a vehicular complement to early-’90s sturdy beats, squared-away flows, and Timberland footwear.

“You’re the type of girl that got class and style/Still and all you need the back seat of my Jeep once in a while.” L.L. Cool J, “Back Seat,” 1993.
“Beep, Beep/Who got the keys to my jeep?/Vroooom.” — Missy Elliott, “The Rain (Supa Dupa Fly),” 1997.
“So don’t sleep when my Jeep creeps up, how we hit ‘em/Empty the clip, then dip cuz we did ‘em.” — 2Pac, “N.I.G.G.A. (Never Ignorant About Getting Goals Accomplished),” 2004.

1994-present: Lexus (LS 400, LX, coupe)

One of the most successful brand launches of the ’90s, Toyota’s luxury line debuted with the LS 400, a rear-wheel-drive sedan powered by a 4.0-liter 250 hp V8, whose sleek exteriors and cutting-edge features waxed Mercedes and BMW ass in critic polls and became the highest-selling luxury import in two years of its release. Its success shocked Western companies that had dominated the market with a more smoothed-out style and laid-back presentation, signaling a renaissance of flossy Eastern makes known for tighter handling, doper flows, and hardcore baller style—personified by a heavyset Brooklynite who remains the brand’s most consistent celebrant on record.

“They heard about the Rolexes and the Lexus/With the Texas license plates outta state.” Notorious B.I.G., “Warning.” 1994.
“On the Lexus LX, four-and-a-half/Bulletproof glass tints if I want some ass.” Notorious B.I.G, “Hypnotize,” 1997.
“Fat like a Lexus Coupe I’ll rip your troop/Not even Lois Lane could get the scoop.” Notorious B.I.G., “Hope You Niggas Sleep.” 1999.

1995-2004: Bentley

Britain’s renowned luxury marque was covertly purchased by Rolls-Royce in the ’30s and in 1998 sold to Volkswagen, whose German ownership failed to taint the car’s reputation as an emblem of regal English charm. The $300,000 auto arrived on our shores just as rap became music’s main corporate engine, its rhyme presence signifying the conquering of an empire. While a “state Limousine” version was presented to Queen Elizabeth II in 2002’s Golden Jubilee, the line’s most vocal U.S. adherents were less confined by courtly protocols.

“Bentley’s limousine, the front yard streams is full of piranhas/I’m set, a private jet, I drink a lot of Beck’s.” Kool G Rap, “It’s A Shame,” 1995.
“I bust six out the roof of my Bentley Coupe/Head shots so motherfuckers can’t regroup, can’t recoup.” Puff Daddy, “Reverse,” 1999.
“I came in ya Bentley backseat/Skeeted in ya Jeep/Left condoms in the baby seat.” Jay-Z, “Supa Ugly,” 2002.

1998-present: Lincoln Navigator

Ford’s largest luxury SUV and Lincoln’s first four-wheel-drive vehicle was introduced in 1997 with a 5.4-liter Triton single-overhead-camshaft V8, fine wood, leather and carpeted interiors, a state-of- the-art marketing squad and the most eager branding participants in music history — some of whom actually joined the design team. “Sean John navigators will be all black with Sean John emblems. They will sport big wheels, tinted windows, satellite radio, three DVD players, six TV screens, a Sony PlayStation 2, heated and vibrating front seats and a designer clock,” USA Today reported in 2003.

“Feds tried to get me you know they some haters/I said ‘See you later,’ jumped in the Navigator.” C-Murder, in Snoop Dogg’s “DP Gangsta,” 1998.
“If the Navi outside, I might be there/Back hoodie, black 9, Black wifey Airs.” The Game, “Money Over Bitches,” 2005.
“Spent a mil’ on the wheels custom wit’ the Navi/Two of the same whips we doin’ it big livin’ lavish.” Birdman in Lil Wayne’s “You Ain’t Know,” 2007.

2000-present: Cadillac Escalade

After a shaky debut in 1998, this second-generation SUV was resurrected in 2001 with standard rear-wheel drive and a 5.3-liter V8. Within three years, enough stars were buying it to boost the average family income of Escalade owners to $150,000—$30,000 more than that of a typical Cadillac family. It was an automotive bookend to rap’s peak years of yuppie conformity. In 2004, Cadillac invited hip-hop artists and athletes to share design ideas at a secret meeting. “We were amazed at the number that accepted,” Cadillac spokesman Jeff Kuhlman said.

“In the sun or up in the shade/On the top of my Escalade/Maybe your girl and my friend can trade.” Ludacris, “What’s Your Fantasy,” 2000.
“I ride down the block in an Escalade/Bling-bling all in your face/I think you might need to put on your shades.” Missy Elliott, “Lick Shots,” 2001.
“Would you like to ride shotgun in the Escalade?” Kanye West, “Wouldn’t You Like To Ride,” 2005.

2002-2006: Humvee

Named for the acronym High Mobility Multipurpose Wheeled Vehicle, this four-wheel-drive military vehicle now produced by GM made its combat debut in the 1989 invasion of Panama. It became the main ground transport of U.S. forces across the globe, a missile platform and a sturdy icon of military might. By 2002, the rounder, roomier H2 had become a status symbol for newly successful rap superstars hoping to project strength and avoid gunshot wounds, their most avid celebrant a bullet-riddled former crack dealer turned squad leader of the paramilitary group, the G-Unit.

“I said I’ve been doin’ my own thang/You can tell by my Benz, by my BM and my Hummer, damn.” 50 Cent, “Doin’ My Own Thing,” 2006.
“I need a drop for when it’s hot/A Hummer when it’s cold/An ill attorney’s in my corner when these fake niggas fold.” 50 Cent, “Too Hot,” 2002.
“Laying with bugs under my shirt, I got plans to hop up in that Hummer/’Cause I’m a stunner, I sit back and wonder/When them angels gon’ call my number.” Lloyd Banks in 50 Cent, “Don’t Push Me,” 2003.

2003-present: Maybach

Mercedes-Benz produced the Maybach 57 S in 2005 and gave it a more powerful 6.0-liter V 12 bi-turbo engine than previous models. Since it also comes with a handcrafted finish and myriad options, each car is one of a kind. At $300,000,it’s almost as pricey as a personalized jet, “but is still more likely to be seen in a music video than on any actual streets, where only around 5,000 were sold in 2004,” notes brand consultants Agenda. Its central place in the hip-hop imagination has made it the Sasquatch of referenced automobiles, or as marketing guru Lil Wayne would put it, an “urban legend like a black Acura.”

“Yeah, ma, your dude is back/Maybach roof is back/Tell the whole world the truth is back.” Jay-Z, “Change Clothes,” 2003.
“Some of y’all caught my feelings from way back/Others waited till I came through, short willing the Maybach.” Fabolos, “Now Ride,” 2003.
“Realest shit I ever wrote, chillin’ in my Maybach/Eight-track episodes, been doin’ this since way back.” Jay-Z in Rick Ross, “Maybach Music,” 2007.

2011: Chrysler 200

Released in 2011, this mid-size sedan gave its predecessor the Sebring a new name and largely cosmetic changes. Retaining the Sebring’s 2.4 L four-cylinder engine, with optional four- or six-speed automatic transmission, the 200 added a new 3.6 L V6 with six-speed automatic transmission, retooled suspension, high-performance tires, LED lighting, noise-cancelling technology, and the angriest spokesman of any automobile ad campaign in history. Six years earlier, a smiling Snoop Dogg appeared in a commercial beside Chrysler hero Lee Iaccoca. During the 2011 Superbowl, Detroit’s leading musical export, whose rhymes have celebrated American-made brands with women-stuffed trunks, piloted a black 200 through the wreckage of the city, stood before a gospel choir, glared at the camera and virtually dared America to buy Chrysler’s new model.
“This is the Motor City. And this is what we do.” — Eminem