The culture of Hip Hop is a hodge podge of different elements that form to make up the lifestyle as we know it. One of these components is the world of athletics. We watch, debate about, emulate, and revere these teams and players as if we knew them personally. During the inception of the Hip Hop generation we have seen many talented players, but there a few that I believe hold a special place in our hearts above the rest. They embody the swagger, confidence, skill, fashion sense, and all around personality that we all recognize and claim as our own. I’ve decided to compile a list of the Top 20 Athletes that I feel have defined the Hip Hop generation over the years. The list is in no Particular order numerically, but rather just a roll call of athletes I feel are deserving of being placed on this list. So, without further adoo, here is PleaseDontStare’s Top 20 Athletes of the Hip Hop Generation.

1. Muhammad Ali

Before the lifestyle that is Hip Hop was ever thought of, there was an ambitious pugilist out of Louisville, Kentucky that was laying a blueprint of swagger and competitive boasting that would be used for generations to come. Even though most of the younger generation wasn’t even born in time to see his magic in live time, he is still revered as an Icon to the Hip Hop community and most are guaranteed to cry like babies whenever he has to leave us.

2. Michael Jordan

There’s probably nothing I can say about dude that you probably didn’t know. 6 NBA titles (6 Finals MVP’s to go along with them). 5 Regular season MVP’s (in an era with Magic, Bird, Hakeem, Isiah, Ewing, need I list more?). All Star games galore, you name it, Jordan achieved it. Add in the fact that he is arguably the greatest player in the history of Hip Hop’s most beloved sport. Not to mention his sneaker franchise is the G.O.A.T. The swagger, the drive, the confidence, it all came together to form the makeup of arguably the most influential athlete in modern history, nonetheless the Hip Hop generation.

3. Allen Iverson

If you were an old white lady or unfamiliar with sports in general, looking at the pic above of Allen Iverson I’m sure she would assume he was a rapper if questioned lol. Ever since he first dazzled die hard hoop fans as an electrifying college star at Georgetown University, we all could see that Allen Iverson represented the culture in a way no athlete really had done up to that point. The tatts, the braids, the street cred, the playground brand of ball we had all seen on our neighborhood courts at some point in our life, it was all there for the world to see, accepted or not. Recording a rap album, doing commercial with Jadakiss, and the brutally honest soundbytes did nothing but affirm his standing in the Hip Hop community. Even through the ups (willing his team to the 2001 NBA Finals virtually by himself) and the downs (being forced to finish his career overseas and not as a celebrated veteran) we ALL claim A.I. as our own and I doubt that will ever change.

4. Mike Tyson

If you remember Mike Tyson circa ’86, and not the character that he has become today, then you would be steadfast in your belief that he is INDEED the baddest man in the world. Back when most of us were sipping similac or in preschool, Mike had cats shivering soon as they stepped in the ring. With good reason too, as he seemed to knock everybody he faced out in the opening rounds. During Hip Hop’s initial years Iron Mike (along with Jordan) were revered as god’s in the urban communities and was the talk of every barbershop conversation. The truck jewelry, the savage boxing style he used, his Brooklyn roots, it all embodied the streets on an athletic level. Even with biting off a mans ear (now THAT’S some BK brawling for you! lol), the unexcusable losses, getting ripped of by Robin Givens, and the bizarre soundbytes, Mike is and will always be embraced by the Hip Hop community for the unforgettable moments and memories he gave us.

5. Bo Jackson

If you, or anybody you know was lucky enough to see Bo Jackson in his prime, you knew that he was arguably one of the top 5 most exciting athletes to watch in NFL history. After burning defenses and nabbing The Heisman trophy at Auburn, Bo then went on to up the ante by not excelling in one, but two sports, also achieving success as an MLB outfielder and designated hitter. Also, playing for the Los Angeles Raiders, at the time one of, if not the most beloved franchises in the Hip Hop community didn’t help the hoods love affair with Action Jackson. Known for his gamebreaking plays (remember him running over Brian Bosworth and the Seattle Seahawks in that infamous monday night game?) and legendary sneaker releases (Bo Jackson’s are among the cream of the crop, just ask your local sneaker collector). Even though his professional athletic career only spanned about a decade, Bo Jackson did enough to guarantee his standing in the hearts of the Hip Hop community for years to come.

6. Penny Hardaway

With Jordan’s first retirement and the league in need of new super stars to further the NBA brand, Anfernee “Penny” Hardaway filled the void effortlessly. Coming off of an All American career at Memphis, Penny teamed up with Shaq to make the Magic the unofficial Hip Hop basketball team of the mid 90′s. With comparisons to Magic Johnson for his height at the point guard position and a flair for still getting his at the offensive end, Hardaway quickly turned into a perennial all star and hood favorite. With his jersey and signature shoe flying off of the shelves and the famous “Lil Penny” commercials, Penny was a guy that could do no wrong. His rise to the top also coincided with the pinnacle years n Hip Hop, leaving him embedded in the nostalgia that often surrounds that particular time period. Even though his career was eventually plagued by injuries, Penny is still one of my personal fave players of all time and if nothing else, his shoe puts him on this list as it is still hailed among the holy grail of sneaks, even though he hasn’t played a noteworthy season since around 2000.

7. Michael Vick

Coming off of an amazing collegiate career at Virginia Tech, most mainstream analysts and critics were put off by Mike Vick. To start off he was one of the first run first QB’s to emerge as a true star, when most people were more comfortable with a standard pocket Quarterback. Then to top it off the braids, entourage, and questionable character issues all cast the Newprt News VA native in a bad light. But the Hip Hop community?? We embraced these “supposed” flaws and most championed him as “Hip Hop’s Quarterback”. We loved the swagger and the 5 on 5 pick up football style he helped popularize in the league. The tatts, the braids, showing crew love, it mirrored us and we could relate to how it effectively made society view us. Even though some of his “crew” was the reason for his eventual brush with the law, most of us never judged him and awaited his return to the league with anticipation. Even though he has toned down his image a bit since his incarceration, he is still revered none the less as the hood’s favorite and will be for many years to come.

8. Shaquille O’Neal

Shaq came in the game and was immediately revered as a larger than life figure on the court. With a big personality and the game to match it, Shaq was rivaling the popularity of Jordan at the time, which at the time was astonishing, but deserved due to his ease in front of the camera and his highlight reel dunks. He was also vocal about his love for Hip Hop and even claimed to be a breakdancer in his hometown prior to his basketball fame. If you were a mid to late 80′s baby like myself, Shaq was probably one of the first superstars you can actually remember seeing enter the league and watching his career throughout your youth and teens. He was also a dream for marketing execs, with them tapping him for various ads and putting his name and likeness on sneakers, video games, movies, etc. Even though we couldnt fux with them sneaks too much (though I have to admit to having owned a pair coming up smh), his Shaq-Fu video game got major play on our Sega’s and his album, the first such foray into music I can remember from an athlete, DID go platinum, which is something you can’t say for any athlete thus far. Throughout his illustrious career (which includes championships, MVP’s, etc), Shaq has always remained loyal to the Hip Hop community and we will most likely always do the same for him.

9. Deion Sanders

You can sum Deion Sanders with just one word…SWAG! In a game where running backs, QB’s, and wideouts’s are usually revered and get all the cool points, Neon Deion revolutionized the cornerback position and kept our eyes glued to the screen whenever a ball was kicked his way. One of the premiere trash talkers and performers in the league, Deion was never one to back down from a challenge and almost always came up on top at the end of the battle. The confidence, TD dance celebrations, the high stepping into the end zone, it all took us back to the days of gathering up the crew for a good ol game of pickup at the park where the trash talk and battles for bragging rights ensued. I’m not even gonna go into the baseball career, which would just be the cherry on top. Championship’s, Pro Bowls, Hall Of Famer, Deion achieved it all for the Hip Hop generation to see and I doubt we’ll find a defensive back QUITE like him in some time.

10. Vince Carter

Even though he has fell off a bit by most standards, from 2000-2003 Vince Carter was arguably THE most talked about and celebrated player in barbershop discussions and blacktop debates amongst the urban community. After enjoying success on the collegiate level at UNC and eventual comparisons to that other UNC high flyer, Carter entered the NBA and immediately made his presence known night after night with his jump out of the gym antics. His signature shoe was cool for a hot sec (BOING!), but nothing to really write home about. What REALLY cemented him as a legend in the urban crowd was his Dominique Wilkins esque domination at the 2000 NBA All Star game, where he did shit NBA legends were even in awe of. The dunk on Fred Weiss ruined homies career before it even started, but that was just for bonus points. Even if he never did anything other than that Dunk Contest Win, he would be good in the hood in my book.

So, there you have it, those are 10 of the Top 20 Athletes Of The Hip Hop Generation. Stay tuned for Part 2 dropping later this week. If you feel I missed anything or have any Hope you enjoyed and let the debates begin!!

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