I love basketball.  I love hip-hop.  But more than anything, I love comparing things that don’t have a fucking thing to do with each other.  So, inspired by the work of Bill Simmons AKA the Sportswriting Jesus, today I am finally unveiling…

My epic project (Part 1) 

Pairing each of the 96 dudes from the Bill Simmons’ Book of Basketball pyramid of the greatest NBA players of all time with a famous rapper based on wholly subjective criteria: Part 1 (#96-62):

96. Tom Chambers – Yelawolf: Tom Chambers was a white boy who flew like none since.  Yelawolf is probably the “least white” white rapper I can think of.  In part cause he covered his skin with tattoos.  But more cause he spits harder than a mafucka. 

95. Jo Jo White – U-God: Jo Jo is probably at the minimum level of “held in revered status” for his contributions to the Celtics dynasty.  Similarly, U-God is probably the least-acclaimed member of the Wu-Tang Clan.  Did you know he quit the Clan at one point, only to rejoin after making up with the RZA?  Yeah, most people don’t know that… or care.  Fair warning: the Celtics/Wu-Tang dynasties are the two most legendary in basketball/hip-hop and I’m taking full advantage. 

94. Jack Twyman – MC Serch: Twyman was a great but not legendary white player who eventually turned into a great broadcaster, as well as being remembered for taking care of his teammate Maurice Stokes after Stokes was diagnosed with a career-ending illness.  MC Serch came up with 3^rd Bass with some other white boys, then turned into a rap talent scout, running reality shows looking for the next great white rapper.  The best rapper he had a hand in help blowing up? He exec-produced Illmatic. 

93. Kevin Johnson – MC Shan: KJ, despite undeniable talent, was pretty much the whipping boy for MJ in the ’93 Finals, the biggest moment of his career.  MC Shan may have been a great rapper, but all we remember him for is getting his ass kicked by KRS-One in the Bridge Wars. 

92. Bob Lanier – Bun B: Bob Lanier is famous for having giant-ass feet.  Bun B’s voice sounds like he should be like 6’7 350 pounds, even if he isn’t.  I always picture him as being like a giant Rick Ross with talent.  Even if this picture says otherwise.

91. Dwight Howard – Young Jeezy: Two freaky talented dudes that you can’t help feeling haven’t reached their potential.  Dwight still doesn’t have that ring, and Jeezy hasn’t had his own hit for a long-ass time.  Still time for both to improve on their legacies tho… and they probably will.  Also, Jeezy’s voice has the same effect on a track as Dwight’s blocks do on opposing offenses.  Fuckin’ intimidating. 

90. Chris Paul – KiD CuDi: For awhile, it looked like CP3 was destined to become one of the all-time greatest point guards in NBA history.  Then, last season, he regressed in basically every single stat and seems like he’s on the verge of pulling a Vince Young.  CuDi dropped one of the hottest mixtapes of ’08 and one of the hottest albums of ’09.  His second album, in 2010, was a pile of shit tho, and now he’s saying he’s gonna become a full-time singer and quit rapping.  What a waste. 

89. Shawn Kemp – Gucci Mane: Shawn Kemp was a physical freak and dirty baller before he lost his marbles and flamed out of the league.  Gucci was a (financially) successful rapper before also losing his mind and becoming a professional defendant.  

88. Gail Goodrich – Missy Elliot: Gail Goodrich is the girliest name in NBA history.  Tho Jan Veseley may give it a run for the money. 

87. Connie Hawkins – Shyne: Connie Hawkins was unfairly blackballed from the league for over half a decade.  Shyne was locked up for nearly ten years, and some people say it’s Diddy’s fault.  IDK, from what I’ve read he was waiving his gun around like Joe Pesci in Goodfellas.  Now he’s living in Jerusalem as a converted Jew.  Really. 

86. Arvydas Sabonis – Fat Joe: Arvydas Sabonis was this giant dude from the USSR with a hilarious name.  Fat Joe is a giant dude who wants everyone to forget he’s not black and has a slightly less hilarious name.

85. Robert Horry – Masta Killa: Horry was the consummate role player who could step up and hit the big shot in the big moment.  Masta Killa would step up and drop hot verses that could push a Wu-Tang joint from great to legendary (like “Triumph”) but didn’t get to star on his own album until 2004. 

84. Cliff Hagan – Rick Rubin: Cliff Hagan was on one of the two teams to ever beat Bill Russell in the Finals.  He was also whiter than the background of a Microsoft Word document.  Rick Rubin was one of the first white producers to really succeed in rap.  And to those who ask, “is it right to factor race into these pairings?  Um, wouldn’t it be more offensive to everyone if I called John Stockton “the Afrika Bambaataa of basketball?” 

83. Vince Carter – Xzibit: Remember when X was dropping all those hot verses on Dr. Dre and Eminem albums, then pretty much quit rap entirely to focus on hosting Pimp My Ride?  That’s pretty much what Vince Carter did with his basketball talent. 

82. Chris Mullin – MC Ren: Chris Mullin is probably the least-remembered member of the Dream Team.  MC Ren is the “oh what happened to him?” MC from NWA.  Best known for their more talented teammates, fairly or unfairly. At least in my mind, and really, not much else counts on this list.

81. Dave Bing – Ice-T: Dave Bing was one of the first stars of the post-merger NBA.  Ice-T is considered the first gangsta rapper.  Neither is really considered a legend and both are actually probably a little overrated.  But Bing made a lot of cash in other business ventures after his career, and Ice-T is making bank on Law & Order.  Way to play, Cop Killer.

80. Bailey Howell – Thirstin Howl III: Look, if I haven’t heard of a dude, and there’s a rapper with the same name, they get paired.  Especially when they both belong on Gilligan’s Island. 

79. Bobby Dandridge – Styles P: Like P on the LOX, Bobby Dandridge was an important contributor for a great team, the ’78 Bullets, even if nobody is calling him the best on the squad (Wes Unseld for Washington, Jadakiss for the LOX). 

78. Paul Westphal – Paul Wall: I mean, they have basically the same name.  And they’re both white, so… there you go. 

77. Dan Issel – Craig Mack: Dan Issel was a hideous dude missing like four teeth.  Craig Mack was a rapper signed to Puff Daddy’s Bad Boy Records, whose career never took off because he was too ugly.  Seriously, when you’re the ugly one on a label with Biggie Smalls, you’re fucking ugly. 

76. Artis Gilmore – Afro Man: Look.

75. Tracy McGrady – Lupe Fiasco: T-Mac was an NBA scoring champion with a wicked cool nickname who could never get his shit together in the playoffs and never made it out of the first round.  Kind of a whiny bitch.  Lupe was one of the most talented Midwesterners to ever pick up a mic and also had a wicked cool nickname.  He never managed to translate his talent into a truly classic album, though, and is also a stupid whiny bitch. 

74. Joe Dumars – Q-Tip: Joey D was a great player who won Finals MVP in ’88, and the front office exec who built the ’04 Pistons champs.  Q-Tip was both one of the MC’s who built the A Tribe Called Quest brand as well as the producer who put the beats together for them to flow over in wicked chill style.  Worth noting that Dumars was about the only person associated with the Detroit Pistons at any point during the 1980’s who could even remotely be described as “chill.” 

73. Sidney Moncrief – Papoose: Moncrief’s career never truly blossomed completely cause of knee injuries.  Papoose’s career never truly blossomed cause his record label fucked him.  Or something.  Either way, two cases of tremendous, unrealized potential. 

72. Chris Webber – Rick Ross: Whenever I think about either of these guys, my first reaction is to laugh.  I mean, C-Webb was the #1 high school recruit in his class, and then made the stupidest play in college basketball history.  Then he was the #1 overall pick in the NBA Draft, and never won a ship or reached his potential.  Rick Ross is just straight up delusional.  He thinks a)he’s the biggest boss in hip-hop b)people take him seriously as a rapper and c)it’s cool to put spinners on a wheelchair for your video.

71. Lenny Wilkens – Pete Rock: Lenny was a great baller but is mostly remembered as one of the all-time winningest coaches in league history.  Likewise, Pete Rock dropped one of the all time classic hip-hop records of all time, “T.R.O.Y.” but is best remembered for his work as a producer.

70. David Thompson – AZ: David Thompson came into the league and was just flying over everyone, then he blew out his knee, and that was that.  Likewise, AZ introduced himself to the world on the only guest spot on the best rap album of all time, Illmatic, with a lot of people saying his was better than Nas’ verse on the same song.  Then he dropped his debut album without much fanfare, The Firm flopped, and that was also that. 

69. Dennis Rodman – Ol’ Dirty Bastard: The craziest basketball player of all time and the craziest rapper of all time.  Dudes were on some nasty squads too, with Rodman winning 5 rings between Isiah’s Bad Boy Pistons and Jordan’s Bulls, and ODB repping the Wu. 

68. Pete Maravich – Eazy-E: Pistol Pete is credited with starting a lot of the tricks in modern ball that didn’t exist during the 50’s and 60’s.  Eazy-E has been called the “father of gangsta rap.”  Neither of these guys was as good you’d think just based on the way everyone creams when they talk about them, but they’re undeniably badass. 

67. Earl Monroe – Dres: Earl the Pearl was a beast way back in the day, but was more or less forgotten by subsequent generations until Denzel Washington did that whole monologue about him in He Got Game.  Dres, the better half of Black Sheep, was too a forgotten soul before “The Choice Is Yours” was featured in that Kia commercial with the hamsters.  Now, I crank that shit everyday. 

66. Adrian Dantley – Waka Flocka Flame: Dantley played ugly, pretty much just knocking dudes out of the way with his fat ass to open up some space to score.  That’s pretty much the way Waka Flocka Flame approaches rapping.  But hey, it works (though I’ll admit that at least 13 of the 17 songs on Waka’s album are complete shit.  But “No Hands” and “Hard In Da Paint?”  Those are staples of the Vandy 311 soundtrack every Friday and Saturday night). 

65. Alex English – Saigon: Big Al once starred in a movie that was so bad it was good (according to Mr. Simmons. I never saw it) called Amazing Grace and Chuck.  Saigon once guest-starred on Entourage, a show that used to be good but is now bad.  And that’s about all anyone knows about him outside of the depths of hip-hop’s underground/HBO.  Seeing as he almost got Drama killed (one of two characters on that show who’s been funny all the way through), he probably deserves it.

64. Jerry Lucas – Ludacris: Lucas was “infamous” (to use Simmons’ description) for padding his stats by chasing down last-second shots for rebounds.  Ludacris has been doing all he can to pad his sales and Google hits by collaborating with Justin Bieber.  What the fuck, Luda?  I hope you smoked him up at least.  The idea of Justin Bieber stoned makes me laugh, and would make a lot of little girls cry, which makes me laugh even more.

63. Ray Allen – Mos Def: Bald dudes who are calm and deadly at the same time.  Also, Ray gave one of the best lead acting performances of all time by a pro athlete as Jesus Shuttlesworth in He Got Game.  Mos Def is one of the most critically acclaimed rappers-turned-actors of all time.  See #62 for more.

62. Reggie Miller – Talib Kweli: Reg is one of the all-time great, stick-a-dagger-in-your-heart long-range shooters.   Talib is one of the all-time great, stick-a-dagger-in-your-heart-with-on-point-lyrics straight-shooting MC’s.  Kweli is one half of Black Star with Mos Def.  Which one’s better?  I think most people would say Mos Def, even if they wouldn’t have back in ’98.  Likewise, Reg vs. Ray Allen is the debate for the best 3-point shooter of all time.  Which one’s better?  I think most people would say Ray, even if Bill Simmons didn’t back when his book came out in ’09.  He later revised that and switched the two for the paperback.

100 swag points for whoever made it all the way here.  This will get even better as we approach the top.  I promise.  Check back (and follow if you haven’t already) for Part 2. 

Deuces