There has always been this natural, cozy connection between hip-hop and basketball. Just one of those pairings that make sense, in an unexplainable yet explainable way. From Chuck D. shouting out Charles Barkley to Phife Dawg name-dropping Scott Skiles to Tunechi making an entire song dedicated to Kobe Bryant, the two just feel right together—like peanut butter and jelly, or Liberals and Birkenstocks. But sometimes things get taken too far. MCs writing clever lines about players is great, having musicians participate during All-Star Weekend is … interesting, but giving NBA guys a microphone and letting them loose can be perplexing. With the Association tipping off this week, here's a look at some of the most memorable NBA players who thought that rap was easy.—Joseph Manuel & Eric Diep

Jason Kidd

Standout Song: "What the Kidd Did"
Best Line: "Don't sweat it everything's gonna be alright / Yeah the people wanna know what the Kidd did / But all you really need to know is I'm tiiiiiiighhtt"

If you've ever listened to Jason Kidd talk during press conferences, odds are you've noticed that he says "You know" about every seventh word or so—and if you haven't noticed before, you'll probably notice now. Either way, it may have been better if he gave us a couple of "You knows" during his debut track, "What the Kidd Did," instead of the jumbled whatever that he spits (although he does drop us a pretty good dime with that Jim Kelly from Enter The Dragon line). First off, the beat is decent—it's on some "Ain't No Fun if the Homies Can't Have None" shit—but hearing Jason say "the hos treated me different" is just … weird. It's Jason Kidd. He's a nice guy. He sprints to lend his teammates a hand to help them up when they've fallen. He oozes confidence and makes locker rooms healthier with his presence. Again, it's just weird. But hey, he tried. And for a top five point guard of all-time with the second most assists ever, his ability to pass really made the game all the more fun for his homes.


 

Gary Payton

Standout Song: "Livin' Legal And Large"
Best Line: "And that's real we all know the deal / And for all those that criticize / I'm not trying to be Shaquille"

Gary Payton can spit. For real. The man was just born to talk. The hardest working mouth in the NBA during his time is actually not a piss-poor master of ceremonies. For all the trash that he talked on the court, it's surprising his track wasn't a diss song aimed towards the likes of John Stockton. But instead, GP gives us a pretty decent look into his ability to flow, almost-maybe-kinda-sorta sounding like a lesser version of Warren G. It's surprising that "Livin' Legal And Large" wasn't already the name of a song, but the Glove locked that down and kept the whole track pretty clean and positive, which is surprising since we're pretty sure the things he said to opponents on the court was not in fact, pretty clean and positive.


 

The Blazers (Damon Stoudamire & Rasheed Wallace)

Standout Song: "No One's Ready To Deal With Us" (No Escapin' This Remix)
Best Line: (Damon Stoudamire) "Go left, go right, 360 degrees / Here comes the pain, Kobe (Pippen and he's poppln' a three!)"

This song is a puzzle. How the hell did the Beatnuts get Rasheed Wallace and Damon Stoudamire in the booth? You've all heard "No Escapin This," but the remix might be hotter, especially since Damon and Roscoe take shots at the Lakers, whom every Trailblazer fan hates more than anything you've ever hated in your life. It's almost unfair to include them on this list since they rapped alongside legitimate, real hip-hop artists, but the track is too solid to leave it off. There are so many gems on this cut it's hard to break it down, but a highlight is his Arvydas Sabonis line, which was probably the best Sabonis lyric ever recorded until Vince Staples dropped "Versace Rap." The samples of Blazer announcers calling games is a terrific touch, and again, the Laker hating makes this a classic Portland gem.


 

Kobe Bryant

Standout Song: "K-O-B-E" Featuring Tyra Banks
Best Line: "Can't get witcha, when the door hitcha, when the Lord splitcha / I figure, hour-glass figures could be dangerous / Cause if your times runs out, they frame you for your clout"

Magnify Michael Jordan's failure at baseball times twenty four thousand, and you have Kobe Bryant's rap career. You've all heard the hot garbage that is Mamba on the mic, but a list of rapping basketball players would be completely incomplete without Number 24. There's really not much to say here about this song -- just picture Kobe's decorated, spectacular NBA career, then picture the exact opposite. But hey, he was on top of the world around this time and in his early 20s, so why the hell not? It's too bad Brandy couldn't have given him music advice when he took her to the prom. Vino gets a pass here for this mishap though, because after all, he has given us great, great basketball moments.


 

Kevin Durant

Standout Song: "Wired (Paid in Full)" Featuring Privaledge
Best Line: "I keep it chill, yeah I keep it chill / Man I'm looking like a prince / While I'm thinking I'm Uncle Phil"

If someone told you about a song by "Trey Five" and you heard "Wired (Paid in Full)," you probably wouldn't think it was Kevin Durant. KD is a unique superstar—he's complacent with Russell Westbrook legitimately thinking that he is better than Durant, he keeps a pretty low profile for the caliber of star that he is, and he plays in Oklahoma City, of all places. Trey Five is pretty solid with his flow—he doesn't seem like he's trying too hard, and he's not waxing poetic about how mean the streets of DC are. He even throws in a Cash Money Millionaires-type lyrics about having a "Roley" and not even needing to know the time. Even though he's arguably the second best basketball player alive at this moment, more heat from Trey Five wouldn't be a total disaster.

Carmelo Anthony And The Denver Nuggets

Standout Song: "Christmas In Hollis"
Best Line: "Don't forget Rudolph, in Christmas apparel / And each and every year we bust Christmas carols"

This is cute. Before Carmelo returned back to The Big Apple, he was in Denver, wearing braids and writing wicked lyrics. All right, so he barely spits on this one but still, it's Carmelo Anthony rapping, kind of. Even though this isn't a real song and technically shouldn't count, it's still notable since Birdman is on it. Oh, and Shelden Williams should probably destroy all copies of this.


 

Brian Shaw

Standout Song: "Anything Can Happen"
Best Line: "Yo when you lose I pay my dues / cause someone's always trying to stop ya / just to get the rep that they got ya"

Brian Shaw sounds like a true OG on this one. Another one of those super West Coast beats, Shaw basically keeps it real and kicks actual knowledge about life—you can legitimately say this song doesn't have a single wack lyric. Who knew Brian Shaw was so smooth? He was only 28 when this dropped, but he rhymes like a well-seasoned veteran, bemoaning the loss of people who were claimed by the streets. Nothing but real, actual praise for "Anything Can Happen." Oakland stand up.


 

Iman Shumpert

Standout Song: "Anarchy" Featuring PhlyyB
Best Line: "Two and one, who is son? I always get it done / Every track is red rum, backwards rule of thumb"

Iman Shumpert wearing a Carmelo Anthony jersey is ______. Part of it makes sense—rappers don't wear jerseys of dudes who average less than 10 points a game. Regardless of what he's wearing, Shumpert may be the closest thing to a real, breathing, hip-hop musician that is also a professional basketball player. His flow is well paced—while you're still comprehending the line he just spit, he's already on to the next one. The beat is solid, with drums reminiscent to that of Tunechi's "A Milli," and Iman just kind of looks and acts the part of a rapper. Also, the fact that he says he's a sneakerhead completes this glorious trinity of basketball, hip-hop, and sneakers.


 

Chris Webber

Standout Song: “Gangsta! Gangsta! (How U Do It)” Featuring Kurupt
Best Line: “Fetish for lettuce from the home of J-Rose and Jerome Bettis”

At one point, Chris Webber exchanged his hoop dreams to be a rapper. He was actually successful, too, with his 1999 debut 2 Much Drama scoring him a top ten record with “Gangsta! Gangsta! (How U Do It).” You wouldn’t expect anything less from an NBA player who produced his own album and wrote his own rhymes. In the song, C-Webb shouts out some homies and tells us how to live lavish. Too bad he couldn’t get more cameos in the video that was supposedly unreleased. The co-signs are everything here. What up Ghost! What up Red!


 

Ron Artest

Standout Song: “Champions"
Best Line: "My stroke is hole in one / You see the checkered flag / Finish line, here I come, and I ain't gotta brag / I let the trophies do it"

Metta World Peace (formerly known as Ron Artest) still believes he can make it as a legitimate rapper. The NBA’s most menacing player isn’t afraid to back down from a fight, and he uses that same fervor to go in with his pen and pad. With an album and a mixtape under his belt, Artest is probably the most prolific b-ball spitter out today. “Champions” was a celebratory anthem that name checks all the greatest athletes in sports. Compared to his earlier work, Metta World  got the biggest reaction from this one.

Tony Parker

Standout Song: "Top Of The Game" Featuring Fabolous & Booba
Best Line: "The music industry freaked of Paris in the USA"

Tony P. launched his music career in 2007 with his first album that had appearances from Jamie Foxx, Bobba Soprano and Fabolous. Since then, the San Antonito Spurs vet has hung up his mic for good, but there’s still this gem to remember him by. “Top Of The Game” collides French rap with the hardened rhymes of a Brooklyn boy. Surprisingly, it’s not as bad as everyone says it is.


 

Marquis Daniels

Standout Song: "Come Here Nikki" Featuring Dee Boi
Best Line: "No top on the interstate, we get that big money—call it Ricki Lake"

While Daniels isn’t rolling with his Milwaukee Bucks family, he’s out making rap songs with his group 1090 Blok Boyz. Under the name Q6, Daniels went hard on the instrumental, spitting Gucci Mane-esque rhymes about his ice game and money. “Come Here Nikki” was his best single featuring a passable verse by Dee Boi.


 

Stephen Jackson

Standout Song: "Save The Day"
Best Line: “PA raised me, NBA saved me / Who would have known that bouncing balls would have me ballin’ crazy”

Stak5 took a familiar route in hip-hop by flooding the streets with his mixtapes. Trill Mixes, which was hosted by DJ Scream, included a gem called “Save The Day.” Most basketball players get inspiration from riches to write their rhymes, but Stak5 was different. Taking cues from hip-hop’s best storytellers, he spun introspective rhymes about how the NBA got him this far.


 

Allen Iverson

Standout Song: "40 Bars"
Best Line: “You went platinum with a ghostwriter / So in the game you won, you cheated”

How could you not include the great Allen Iverson as the best NBA rapper alive? Ok, A.I. touching on vile topics like homophobia and gun touting doesn’t exactly fit with the NBA’s code of conduct. Still, The Answer tried hard to get some things off his chest as Jewelz in the song “40 Bars.” Not exactly grade-A material, but he had enough lyrical chops to start working on an album.


 

Shaquille O'Neal

Standout Song: "(I Know I Got) Skillz"
Best Line: “I smoke-smoke the mic-mic, I Cheech & Chong you / You don't like Shaq, frankly I don't give a damn / I know I got skills man, I know I got skills man”

As a professional athlete, Shaquille O’ Neal dominated as the big man for the Los Angeles Lakers. When he transitioned into making rap tunes, Shaq Diesel’s reign in the game couldn’t be stopped. He was one of the rare basketball players who got a platinum-selling album, as well as worked with legendary artists like Phife Dawg, The Notorious B.I.G, and Erick Sermon. he was the total package and became successful in both lanes. Salute, Big Aristotle!