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My top five list summer edition continues with the coolest players of all-time. Listen, I think we know the obvious names who would be on list (Julius Erving, Allen Iverson, and Michael Jordan) I did not include on my list and tried to dig for other cool option because adding those obvious icons would be too easy as they are basketball royalty, and their cool factor is written in stone. This list is about the players who had that special something that made them just as cool. So here is my top five coolest players list but here are some honorable mentions.
The Honorable Mentions
Kenny Anderson – Kenny Anderson was pure poetry being one of the original New York City point Gods that electrify the New York/New Jersey area when he was a Net, add that he was also left-handed made instantly cool for me.
Hakeem Olajuwon – The Dream was magical in the post with his amazing footwork, don’t believe me look up the moves he put on David Robinson on YouTube and tell me I am wrong.
Kevin Garnett – KG’s raw, unfiltered passion was undeniable and inspiring for a teenager like me. His loyalty and dedication made him one of the best players of this century as well as a memorable cool player because anything is possible!
LeBron James – LeBron is truly a one of one player at 6’9 250-260lbs built like a power forward but has the mind and vision of Magic and Bird then add insane athleticism with a supercomputer basketball brain we haven’t seen before makes him one of the most electrifying and coolest players who just missed my list.
Shawn Kemp & Gary Payton – Kemp and Payton were one of the duos that defined the coolest of the 90s NBA, perhaps the most iconic or one of them at the least because the Reign Man and The Glove are living definitions of cool.
Charles Barkley – Sir Charles was must-see TV. Never knew what he was going to do or say next, but you knew it was about to be something very in your face and unapologetic while making something like rebounding look badass.
Now on to my top five coolest players of all time!
5. Baron Davis
Baron Davis was that dude who played basketball like he was having a blast and did not care who watched. BD had this swagger where he would pull up from the parking lot, cross you up, dunk on anybody or drain a jumper, then stroll back down court like he placed a door dash order. Do not believe me? Ask Andrei Kirilenko about the poster he was put on in 2007.
What made Baron special was how he made the impossible look casual. The deep threes, no-look passes through triple coverage, dunking on centers, the man played with joy, and that joy was infectious.
4. Sam Perkins
I would not be true to myself if I did not Big Smooth Sam Perkins on this list. At 6’9″, Sam Perkins was pulling up from three when dudes were still figuring out the two-point game. His shot was butter, his demeanor was so cool, and he had this way of making everything look effortless.
Perkins never rushed, never panicked, never broke a sweat. He would catch the ball 25 feet from the basket, give you that little shoulder fake, and then drain it in your face like he was shooting around in his backyard which I certainly tried to copy throughout my life. Sam Perkins was pure finesse, smooth as silk but deadly.
3. Shaq & Penny
One of two duos to my list and the Orlando Magic in the mid-’90s was appointed television, and this duo was the main attraction. Shaquille O’Neal was this massive human wrecking ball who somehow moved like a point guard. Every time he caught the ball, you knew something ridiculous was about to happen, either he was going to dunk so hard the rim needed therapy (being there in person when he broke the backyard in New Jersey was memorable) or some poor soul was about to be a part of some highlight for the Inside Stuff.
Then there was Penny Hardaway who was the perfect sidekick, smooth, creative, and had handles like an evolved Magic Johnson. His passes were art, moves were poetry, and together they made basketball look like the most fun you could have and spoke to a whole new generation of young fans. They were young, talented, and played with this infectious energy that made you want to grab a ball and hit the court, lower the basketball, and try to bring the basket down.
2. Vince Carter
My number 2 coolest player of all time may shock a lot of people who know me because he could easily be number one, but Vince Carter was something different and exciting especially for a raptors fan like me. To say Carter could fly is an understatement! Imagine hang time like MJ, Coolness of Dr. J, and the explosiveness of Dominque Wilkins cranked up to 100, VC brought theater to basketball. Every time he touched the ball, something magical might happen. He would catch a lob and somehow find a way to make it more spectacular than physics should allow. His dunks were not just powerful; they were aerial masterpieces.
But Vince was more than highlight reels. He had that cold-blooded confidence, that “I’m that dude” swagger that made everything look easy. Three-pointers, fade-aways, crossovers, just had style. The man simply made basketball look like a video game that included clearly a 7’3 center for the most memorable in game dunk we will ever see during the 2000 Olympics that was so ruthless that center never got on a plane to come play in the NBA, I wonder why.
1. Anthony Mason & Charles Oakley
This is where basketball gets real and to me simple. Anthony Mason and Charles Oakley were not just players; they were the embodiments of New York basketball. They controlled games through sheer presence and will.
For me being a chubby kid, Anthony Mason was built like he was chiseled from stone, with that perfect flat-top and arms was different, but don’t let the muscle fool you with Mase who had soft hands, court vision that could thread needles, and handles that broke people’s brain. He would grab a board, push it up court himself, and find the open man with a pass that made you rewind the tape.
Then there’s Charles Oakley the enforcer, the protector, the guy who set the tone for everything that happened on that court. Oak did not just play defense; he made offensive players reconsider their life choices. But he did it with this quiet, professional confidence that was somehow scarier than all the trash talk in the world while making rebounding and owning the glass be one the coolest parts of basketball.
Together, they were untouchable. They did not just play basketball; they owned every square inch of hardwood they stepped on. That is not just a skill that is pure, undiluted cool. That is New York basketball at its finest. And yes I was that kid who wanted various designs or his name in his head like Mason and did so from the Nike swoosh to the WWF logo to my name were cutting into my head in second, third, and fourth grade that every once in a while may still happens in my adult life (laughs).
Basketball is supposed to be fun, and these players made it feel like the coolest thing on Earth. That combination of skill, swagger, and style that made every game feel like an event. They were not just playing basketball; they were putting on a show, and we were all lucky enough to see these players during the most popular time for basketball that their coolness still resonates well into today.