It’s like Drake said on Thank Me Later’s “Thank Me Now”: “Damn, I swear sports and music are so synonymous/ ‘Cause we want to be them, and they want to be us.” Drizzy wasn’t the first to say it, though, and he won’t be last. Hoops and hip-hop have had a casual relationship since before Shaquille O’Neal picked up a mic in ’93 — a relationship that became much more serious when Allen Iverson entered the NBA in ’96. The relationship continues today, with Lance Stephenson and Damian Lillard dropping new music just this summer. Aside from the obvious link of both forms courting black men from impoverished neighborhoods, there’s something else, too: The ego it requires to be either the one of .03 percent of high school players who makes it to the NBA or an accomplished rapper with even a decent career must know no bounds. Excessive hubris can be a detriment, but when it makes society’s longest, gangliest multimillionaires move and speak awkwardly to beats, the result is often more comical than sad. In honor of the off-season being officially underway, the summer leagues coming to a close, and NBA players having much more time to explore the non-basketball aspects of their lives, let’s take a look at the best and worst of those who decided to step off the court and into the recording booth.

17. Tony Parker

When you have more NBA championships than decent songs and yet you are nowhere near Bill Russell’s 11 rings, it’s a pretty good indicator that you shouldn’t rap. Yet Tony Parker only announced his retirement from the rap game in 2013 after six years, an album, and a handful of singles. 2007’s TP is a frontrunner for the worst “raplete” album of all time. Granted it is in French, so I can’t tell if the lyrics are particularly good, but his flow and delivery are so off that it doesn’t even matter. French rap in general has a disregard for staying on beat, but Parker takes that to a whole new level … unintentionally. Jamie Foxx is the most well-known feature on the album, and the production is typical of most French rap — late-’90s leanings with a surprisingly well-chopped sample every now and then. (Parker somehow landed Fabolous for a single as well.) Parker also spit a freestyle in French during the Spurs’ 2007 Championship parade, and that is most likely the loudest applause he’s heard from an American crowd off the court, but even those cheers were a bit awkward, with Brent Barry and Bruce Bowen serving as unofficial backup dancers. Any team would rather have Metta World Peace perform at their championship parade if given the choice, but what a decision to have to make.

16. Steve Francis

It’s a shame about Steve Francis. The former Rookie Of The Year and three-time All Star fizzled out of the league after averaging a solid 18 points and 6 assists for his career. Francis was one of basketball’s brightest stars, and it seemed he was headed for the Hall Of Fame, but instead, he was trying to start his rap career at 35 years old in 2012. No full-length project ever surfaced, but a single and matching set of visuals was released for his one and only song, “Finer Things.” There is no redeeming quality to this song or video. Francis’ off-key singing on the hook and a reckless disregard for staying on the humdrum beat make the song unlistenable. The video is simping 101. Francis wins a woman over with his flashy lifestyle: private planes, jewelry, etc., and even has some kids (presumably the woman’s, maybe his?) eating an expensive dinner with them, just shelling out money all over the place. It’s refreshing to see an atypical relationship in a rap video, but the visuals just don’t fit with the awful song. One can only hope Francis is finding his way, staying out of strip clubs with Drake, keeping his chain tucked, and not wasting his time convincing TMZ cameramen that he could still play in the NBA.

15. Delonte West

Delonte West was not merely an average NBA player, nor was he your ordinary person. West was diagnosed as bipolar by a specialist in his hometown of P.G. County, Maryland, in 2008, and displayed some idiosyncratic behavior that made a lot more sensee after the diagnosis. This behavior includes being pulled over while speeding on a three-wheeled Can-Am Spyder motorcycle with a .357 magnum, a 9mm Beretta, and a Remington 870 shotgun in a guitar case; interviews that would make you cringe from the extreme awkwardness and lack of tact; and an alleged affair with then-teammate LeBron James’ mother. Yet 2011 was perhaps West’s shining moment as he played the comic-relief role for the pointless, prolonged NBA lockout. Many players explored the non-basketball aspects of their lives during that time, but none did it quite like West. Before applying for jobs at Home Depot and wholesale store BJ’s, becoming Regency Furniture Showrooms’ most famous delivery man, copping an “O.J. Simpson-style” white Ford Bronco, and keeping the Twitterati mesmerized, he leaked a few tracks from his unreleased mixtape, Lockout, under the moniker Charlee Redz. A Desperado-esque, steel-toting, motorcycle-riding, alleged literal motherfucker seems like the ill rap persona, but the lifestyle did not transfer to the music. The technical sound quality of the tracks is the highlight, as it seems West built a pretty good home studio. But the rhymes are boring, elementary, and slightly off-beat, and the beats are just generic trap. His biggest “hit” was “Livin’ Life Fast,” which he actually knew a little something about, but the video featured footage of him playing a racing video game at an arcade instead of whipping that O.J.-style Bronco. West still hopes to play in the NBA again, after stints overseas and in the D-League. Yes, pick up the ball again, but rent out that home studio to someone else.

14. Kobe Bryant

Kobe Bean Bryant is a future Hall Of Famer, and to most NBA fans, a living legend. Some consider him to be the best shooting guard of all time, but Michael Jordan is still regarded by most as the G.O.A.T. Much of Kobe’s on-court swagger, moves, and disposition came from Michael, as it is fairly well-documented that Kobe studied tapes of MJ in his youth while developing his game. Bryant the rapper similarly lacks his own steez. His approach to the rap game was simply awkward. His debut album, Visions, never saw the light of day, and it is most likely because the lead single, “K.O.B.E.,” featured Tyra Banks. Banks is not the worst vocalist, but when trying to launch a music career it would most likely be in your best interest to use your prom date, Brandy, instead of a model-turned-singer who was also trying to diversify her portfolio. That said, the second single, “Thug Poet,” is just laughable, as Bryant is neither a thug (not that that’s a good label) nor a poet. The lack of swag, questionable moves, and existing in Shaq’s humongous 7-foot-1 shadow in both rap and basketball early on blinded Kobe’s Visions, but Kobe and hip-hop are better off for it.

13. Allen Iverson

Allen Iverson, aka AI, aka the Answer, aka Jewels, is the player most cited as responsible for the connection between hoops and hip-hop. Shaq did his thing (more on that later) before Iverson, but no baller authentically embodied hip-hop like the Answer. The tattoos, cornrows, du-rags, baggy jeans, 8XL tees, chains of all varieties, and undeniable swag were all trademarks of #3 for the Sixers. He has been in the top-10 jersey sales five times during his career, and peaked at second behind Kobe Bryant, but his jersey sold just as much for cultural reasons as his prowess on the court. Given all of this popularity and organic ties to hip-hop culture, it would seem Iverson’s transition into rap would be seamless. But his 2000 debut, Jewels, was never released mostly due to backlash from NBA Commissioner David Stern for lyrics fraught with homophobia, violence, and promiscuity. However, it frankly should have never been released just based on how awful it was. Iverson’s lyrics about carrying twin .45s and putting those with “faggot tendencies where the maggots be” were more disheartening than other wannabe gangster rapletes. True fans can remember when AI’s opportunity to play college ball was almost snuffed due to a bowling alley brawl where he was a victim of circumstance and stereotype, and the multiple arrests for drug and gun possession, and domestic disputes that threatened to end his NBA career. When all was said and done, Iverson was just being himself, but it would have been nice had he shown more in his music than what was already assumed about him.

12. Kevin Durant

KD first spoke over a beat on Wale’s More About Nothing mixtape in 2010 on “The KD Interlude.” The track made me wonder if he had any rapping skills since he was chilling with rappers and got some space on a good mixtape. Then “Worried About Tomorrow” surfaced in 2012, and my inkling had been confirmed. Durant can actually ride a beat pretty well, and he managed to maintain his down-to-earth image on the track, as it’s mostly about trying to stay humble in the midst of signing eight-figure contracts and being an international celebrity. KD seems like a modest dude from D.C., and he is much too concerned about winning his first championship ring to make regular trips to the studio. So rap is most likely not in the cards for him, but I could see him starting a label or investing in the music business behind the scenes.

11. Marquis Daniels

After going undrafted in the 2003 NBA Draft, Marquis Daniels has a had a decent NBA career, averaging just under 8 points a game and contributing to four different teams as a solid defender with a reputation as a team-first type of player. He has been described by his teammates as being quiet in the locker room, and he hasn’t spent much time in post-game interviews as he usually isn’t the focus of any given game. But his rap alter ego Q6, formerly known as Lambo6, will say just about anything over an instrumental. Blood affiliations, women, money, kicks, clothes, drugs, and his native Orlando, amongst other subjects, are all up for discussion. The music is a bit of a throwback as it is mostly characteristic of the early-/mid-2000s Atlanta snap movement and early, basic trap beats. Q6 is what Killer Mike would call “baby shit, just basic boo-boo.” Daniels has collaborated with Lil Boosie and Trina, but mostly he works with what seem to be childhood homies or members of his entourage. Stephen Jackson raps circles around him on their collab, “Boolin.” Daniels has his sights set on coaching in the near future, but Q6 has three mixtapes to his credit and a slew of recent singles, so it seems he isn’t going to stop recording anytime soon.

10. Louis Williams

The reigning Sixth Man Of The Year and recent Lakers signee is at the top of his basketball game. Apparently, Louis Williams’ game off the court is strong too, as he openly has two girlfriends, and the threesome hangs out together on the regular. His rap game, not so much. Williams spent his first seven seasons in the league with the Philadelphia 76ers, and developed a friendship with Philly native Meek Mill. Meek may have encouraged Williams to step into the recording booth, but Williams took more than just advice from him. Williams’ flow and lyrical ability aren’t bad, but he raps exactly like Meek, and clones are never as good as the original. He doesn’t have a mixtape or any other projects out, but he holds his own on a feature with Meek and a collab with Meek and 2 Chainz. A longer project from him wouldn’t be an abomination, but it would most likely float into nothingness.

09. Lance Stephenson

Apparently Lance Stephenson’s trip to the studio for the remix of Bobby Shmurda’s “Hot Nigga” wasn’t a one-time occurrence. Celebrating his trade to the Los Angeles Clippers, Stephenson (aka Born Ready) released “Poppin” in June. It sounds similar to his first song. He spits a couple decent braggadocious verses with the same flow over a murky, piano-driven trap beat with drill leanings. Hailing from Coney Island, Brooklyn, Stephenson attended Lincoln High School, the school that produced the fictional Jesus Shuttlesworth (played by Ray Allen) from He Got Game and Sebastian Telfair. Stephenson’s loose affiliations with Spike Lee and the hip-hop haven of Brooklyn undoubtedly influenced him, but he’s a middle-of-the-road rapper. He won’t elicit feelings strong enough to make you wish he would stop rapping, but it’s not like you’re going to rush to listen to a freshly released track, either. Stephenson is the least talented of the new wave that includes Damian Lillard and Iman Shumpert.

08. Joe Smith

Post-hoop life has been relatively tough for 1995’s first-overall draft pick. Since his last full season with the Lakers and Nets in 2011, Joe Smith has accused now-ex-girlfriend and Love & Hip Hop Hollywood star Moniece Slaughter of duping him out of $109,000, put his $2.75 million home in Arizona up for sale, and is currently building a relationship with his estranged son, Amir, as Amir’s mother has been diagnosed with cancer. In 2009, during the twilight of his career — perhaps in an effort to stave off what he’s going through now and get an early fresh start — Smith released The Beginning as Joe Beast. The 19-track project shows a level of commitment that most other athlete rappers don’t normally reach, but his skill level doesn’t come anywhere close to his dedication. The money-cars-clothes-hoes raps aren’t delivered very artfully and they are downright weird coming from his mouth. Smith maintained a reputation as one of the nicest guys in the league, so the boasts about pulling dozens of women at a time because “pimping is as easy as a free-throw” and his relationships with the “true killers, criminals and murderers, and Pittsburgh Steelers” seem faker than actual rappers who get their mail at a Front Street address. Not only are the depictions unbelievable, but even if they were true, you don’t want to believe them. Also, how much of a gangster mack could you really be if you only come at Donald Sterling and Justin Bieber? The self-proclaimed “voice of the NBA” is pretty quiet now except for random shots at easy targets, but those are preferred over another mixtape.

07. Troy Hudson

Troy Hudson’s rap career mirrored his career in the league. Hence the very appropriate title of his first and only full-length project, Undrafted. T-Hud was doomed from the start. There are no Tom Brady undrafted stories in the NBA where a player watched 60 other guys get selected before him in the draft and then prove himself pivotal in winning four championship rings. Hudson managed to stay in the league for 16 years mostly as a solid backup point guard, and never got the chance to have a regular starting role. He put up decent numbers off the bench and even received a few Sixth Man votes, but was never given the kind of minutes to truly shine. Undrafted is similar because Hudson’s rap skills are decent. He can ride a beat pretty well, and though most of the rhymes are of the nursery variety, there are a few multi-syllable eyebrow raisers. But leftover beats from good producers and throwaway verses from pretty good features like Three 6 Mafia and UGK led to a dismal 78 copies sold. Hudson probably never should have picked up a mic, but he had an interesting story to tell as an undrafted player who earned at least veteran’s minimum for 11 years. It would have been great if he had just told it better.

06. Metta World Peace

Looking up to Nas, Mobb Deep, and cousin Capone of Capone-N-Noreaga in the Queensbridge Projects, the artist formerly known as Ron Artest has been rapping for quite some time. He claims that at age 19 he started a fledgling hip-hop label with the hopes of signing Chingy as his first artist. He released his first album, My World, to deaf ears in 2006 on his Tru Warier imprint after requesting time off from the Indiana Pacers two years earlier to pursue his pen-and-pad dreams. According to MWP, My World included just 21 of five or six hundred songs. Unfortunately, the highlight of his debut project was the vintage Diddy smooth talk on the intro. MWP unintentionally wanders off-rhythm for far too long on almost every song before finding his flow, the majority of bars could have been snuck into See Spot Run! without anyone being the wiser. His delivery is lifeless, especially for such an animated person and player. But did that stop MWP? He went on to use the spotlight of the Lakers 2010 championship to drop some new material, including his biggest hit to date, “Champions.” A certain amount of appreciation is demanded for the improvement from his first album, but outside of Lakers fans giddily dancing to “Champions” at the victory parade, there was no love for the song, and rightly so. Rapper MWP has been quiet as of late, but he was ejected in the season’s final game for his Italian team, so it seems he’s up to his old antics. Hopefully he gets back to educating kids about mental health and devotes his time to maintaining his own.

05. Stephen Jackson

Mr. Jackson, aka Stak5, is quite the legitimate rapper. He spent 12 years in the league, and put in nearly as much time in his basement studio, recording for about a decade before any of his material saw the light of day. Like Delonte West, Jackson used the lull of the 2011 lockout to showcase his off-court passion. Hailing from Port Arthur, Texas, the home of veteran Bun B, Jackson similarly has a deep Southern drawl that is tailored for trap beats. Unlike the majority of his rapping peers, he has the ability to switch flows, and does so regularly from song to song and also within verses. Lyrically, there is no need to rewind for comprehension, but his similes and metaphors are on point. And when he gets into some gangster shit, it’s not that farfetched for those who can recall him punching Pistons fans alongside Ron Artest/Metta World Peace while playing with the Indiana Pacers, choking fellow raplete Steve Francis at a Houston nightclub during a performance, and his generally combustible nature on the court. Jackson has received co-signs in the form of features from T.I., Jeezy, and Texas pioneer Scarface, and his two YouTube accounts boast 29 uploads in sum, including 12 videos that range from quick-and-dirty edits to extended cuts with sizable budgets. The latest upload came about a month ago. Jackson also has a mixtape (2011’s What’s A Lockout) and an album (2013’s Jack Of All Trades) under his belt, and while there will be no plaques to keep his 2003 championship trophy company on his mantle, the guy can spit. As far as NBA rappers and post-NBA careers go, Jackson isn’t doing too bad for himself.

04. Chris Webber

Chris Webber may have the most famous lapse in judgement in sports history, calling a timeout when his Michigan Wolverines didn’t have any left, resulting in them losing a championship that was theirs for the taking. But a close second is his decision to step in the booth in 1999 to record his debut, 2 Much Drama. Webber, aka C. Webb, is not completely devoid of musical skill as he produced “Surviving The Times” on Nas’ Greatest Hits album, and “Blunt Ashes” on Hip Hop Is Dead. The lead and lone single on 2 Much Drama, “Gangsta! Gangsta! (How You Do It),” hit #10 on Billboard’s Hot Rap Singles, mostly for its beat with a sliced Busta Rhymes sample and loop from Laid Back’s “White Horse.” Webber goes bar-for-bar with West Coast veteran Kurupt on the track, with plenty of internal and multi-syllable bursts. Redman makes an appearance on the album as well, and Webber holds his own against him. However, Kurupt and Redman are the only two features, and at 21 tracks, the project gets repetitive quickly, ultimately droning on for far too long. Webber is welcome behind the boards, and he can rap circles around most of his raplete peers, but he should probably hold on to his gig as an analyst at NBA TV.

03. Iman Shumpert

There is more to the flattop than meets the eye. It may be just a haircut to some, but Iman Shumpert lives in Th3 #Post90s. His 2012 debut was on the better end of the spectrum for NBA rappers. His flow and delivery varies, he can rock over trappy beats (“Versace”), early-’90s Das EFX instrumentals, and pretty much anything you throw at him, but it won’t be anything that will particularly stand out. A battle between Shumpert, Damian Lillard, and Lance Stephenson for best of the new-school rapletes would be pretty entertaining, though.

02. Damian Lillard

Damian Lillard tried to play off founding #4barFriday as harmless fun, but the man went too hard in his bars for it to be a mere hobby. The hashtag, which Lillard now calls a community, is now in its 32nd week and has developed into a platform for up-and-coming artists and NBA players alike to put their bars on display. Paul George, LeBron James, and Iman Shumpert are just a few of the participants. Lillard has now moved past the hashtag, first to kill a verse on Sway’s radio show, and then to SoundCloud as Dame DOLLA (Different On Levels The Lord Allows) to release three tracks this summer that are apparently from a mixtape that will drop before the start of the 2015-2016 season. The tracks actually merit some discussion, as Shumpert doesn’t rap about the normal things your average athlete trying to sound like an average rapper raps about. He talks about his struggles growing up in Oakland, how he won’t let the fame and money change him, and he provides a surprising amount of insight into the intersection of hip-hop and hoop culture. Dame displays dexterity and versatility that no other raplete has. His first single, “Soldier In The Game,” is over a trappy beat with a bit of yay area slap laced throughout. It is far more than the title suggests, as he regales with tales of growing up poor in Oakland and his struggles to get to where he is in the league. Lillard also manages to relay these messages through verses jam-packed with unorthodox similes, inventive metaphors, complicated rhyme schemes, and multiple deliveries. The other two singles, “Tell Me Why” and “Full Stomach,” are verses over the instrumentals for Jadakiss’ 2004 single “Why” and Common’s 2008 track “The Food.” Dame’s versions give both originals a run for their money. The acronym for DOLLA is kind of corny, but that doesn’t make it any less true. Dame is different. To have legitimate buzz for a mixtape as an NBA player is rare. Lillard is going to continue to be a problem for fellow point guards and rappers alike.

01. Shaquille O’Neal

Shaquille O’Neal aka Shaq aka Shaq Diesel aka Shaq Fu aka Kazaam aka Superman is easily the most successful NBA rapper to date. He has a platinum certification for his debut, Shaq Diesel, and a gold certification for his follow-up, Shaq Fu: Da Return. He is also the only NBA player to have a recording contract (on Jive Records) and not be forced to start his own or go the indie route. The beats are watered-down A Tribe Called Quest without the genius loop selection of Q-Tip, but inviting for dancing and rapping. O’Neal’s flows are not bad, very typical of the early ’90s, overflowing with energy and Busta Rhymes-esque onomatopoeia. Shaq’s delivery varies, and the subject matter is playful no matter the topic. Hence lines like, “SuperShaqifragilisitcexpiallidopeness.” Shaq has never fancied himself a serious individual, and he has also seen the commercial and monetary value in that since entering the league. Why else would he jam his knees into his chest trying to convince people that Buicks are roomy enough for him? The lightheartedness of his rap persona and the raps themselves encourage fun and inclusiveness. He even made things innocuous enough for kids to get into with lyrics like, “I don’t give a heck.” No, Shaq is not the most skilled rapper, but he was smart enough to know his lane and not swerve. Shaq’s cognizance of his appeal, his smart approach, and his stature as the most successful basketball player to rap easily puts him in a league of his own.