This month marks the 50th anniversary of hip hop, an artform that has touched every corner of Western society. (Even Rodney Dangerfield got in on it.) And of course, 50 years of hip hop bring with them a half-century connection with car culture. From the Pontiac Catalina of DJ Kool Herc (credited as the inventor of hip hop) to Kool Moe Dee’s YJ Wrangler to Eazy-E’s Impala to Biggie’s Lexus, LX, four-and-a-half, the story goes on and on.

That said, one MC keeps on rising to the top when it comes to taste in cars: Jay-Z. As far back as one can tell, Jay had an eye for the right car for the right moment—not just the most expensive thing available. Let’s take a look at a few.

1989 Mercedes-Benz W201 190E

It was 1989 and Sir Mix-a-Lot was rolling Rainier in a stretched Mercedes-Benz W126 S-Class wearing an AMG body kit. Meanwhile, on a trip to London that same year, Jay-Z posed for a photo behind the wheel of a far more humble W201 190E—eco-maximizing aero hubcaps and all. One MC was on top of the world, the other was starting the climb. Admittedly it all works better in retrospect, but the look on Jay’s face says he knows where he's headed.

1996 Lexus GS300

Penned by the great Giorgetto Giugiaro, the first-generation Lexus GS300 was… not a huge success. It arrived in the US in 1993 and was gone by 1997. But come 2006, it made a triumphant comeback. For the 10th anniversary of the album Reasonable Doubt, Jay put together a one night only show at Radio City Music Hall (Part of “Roc-a-Fella” Center! -Ed.) backed by a live orchestra. And how did Jay take the stage? In a white tuxedo—after rolling up in a ’96 GS300. Period correct, but as unconventional as the show itself.

1998 Mercedes-Benz C140 S-Class Coupe

Featured in the video for The City Is Mine, this generation of S-Class—coupe (a.k.a. the CL) and sedan—still have a certain aura about them. Even today, if one’s rolling up on you, there's somebody inside who can and will fire you on sight. A perfect automotive metaphor for what Jay-Z declared on the track: he’d climbed the ladder and was now top dog in the New York rap game. Although a claim of “the city is mine” followed by a chorus declaring “you belong to the city” does beg the question of who belongs to who, or at least who owes what to whom.

1959 Rolls Royce Silver Cloud

While not directly part of Jay-Z’s collection, this 1959 Rolls Royce Silver Cloud deserves a mention as it belongs to his wife, Beyoncé, but is alleged to have been a gift from her husband. There could be other explanations, but it does comport with Jay-Z’s knack for knowing the right car for the situation and/or person. In fact, Bey and her Rolls were just spotted in the Hamptons, with Jay in a Land Rover Defender 110 (with something going on with the rollbars) not far behind. Was it the only Roller at whatever destination Carter & Co. were headed for? No way. But it definitely made an entrance that nothing else could.

1998 Bentley Azure

It’s a hard knock life for any pre-VW Bentley owner, and usually it’s rod knock. But Jay was up for the challenge, and his late-90s Bentley Azure was featured in the video—and eponymous album cover—for Hard Knock Life. Notably, that tile carried the appendix of Vol. 2., making it a successor to In My Lifetime, Vol. 1. That's an important distinction, because whereas the former featured the CL and its story of rising to the top of the game, the latter was about rising above the game. It's about being in a position to acknowledge where you came from without reservation, to enjoy in equal measure a chop cheese and a bottle of Armand de Brignac, to have a more wholistic view on life and the world at large. This is a track written by someone who owns a Bentley. And that Azure is parked for most of the video, so it may be a genuine ownership experience, too.

The life and times of Shawn Carter have taken many twists and turns, and it certainly wasn’t preordained that Jay-Z’s journey from a young hustler to a global music mogul and entrepreneur would be a successful one. But it does seem as though Jay’s car collection was. His choices are personal, purposeful, and contribute to a narrative whole. They have meaning. And that’s part of why we celebrate 50 years of hip hop—and look forward to 50 more.

The History of Hip Hop [via The 50th Anniversary of Hip Hop]