40 Most Entertaining Personalities in NBA History

Josh BenjaminCorrespondent IOctober 19, 2011

40 Most Entertaining Personalities in NBA History

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    Looking through NBA history, there are some people who just stand out.  Some may be hotheads, some may be completely stoic, but what about the ones who are sometimes just downright hilarious and, well, entertaining?

    Keep in mind, this category of people isn't restricted to players.  I'm talking about players, coaches, broadcasters and, in some cases, executives.  It seems that in most generations of the game, there have been a few individuals whose personalities have just had that extra oomph.

    That being said, let's dive right in and look at, in no particular order, the 40 most entertaining personalities in NBA history.

Dikembe Mutombo

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    Retired Congolese center Dikembe Mutombo was entertaining for a couple of reasons.  First, his accent was so thick that something about it just made us smile.

    More importantly, he was a class act with a phenomenal sense of humor.  If there were an NBA award for making fun of oneself, Mutumbo would have won it multiple times.

    Oh, and who didn't love the famous Mutombo finger wag?

David Kahn

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    David Kahn is entertaining because although he has been the subject of tons of criticism since becoming GM of the Minnesota Timberwolves, he brushes it off like water off a duck's back.  The man just doesn't care.  In a league that has very demanding fans, that's badass.

    Keep in mind, we're talking about a man who traded Al Jefferson and signed Darko Milicic to a $20 million contract.  On top of that, he traded for an extreme headcase in forward Michael Beasley.

    Sure, the fans cried foul, but Kahn kept his cool.  In doing so, his indirect message to the fans was something along the lines of, "I'm doing my job.  You focus on yours, which is rooting for the team."

Mikhail Prokhorov

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    New Jersey Nets owner Mikhail Prokhorov entertains me for one reason.  I'd love to figure out how his mind works.  Here is a man who, with a straight face, traded the talented Devin Harris and a rookie with a high ceiling in Derrick Favors for the volatile Deron Williams.

    How does anyone come to the conclusion that trading those guys for Williams is a good trade?  Sure, it may work out in the long run, but to give up a potentially deadly shot-blocker in the process?

    Either way, Prokhorov is slowly making his mark as an owner and will be entertaining fans for years to come.

Shawn Marion

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    If legendary broadcaster Gus Johnson were calling a jump shot by Shawn Marion, it'd probably go something like this: "MY NAME'S SHAWN MARION!  I HAVE THE UGLIEST JUMPER EVER!"

    Seriously, watch the man's shot.  It's like he pushes it up from the middle of his chest and by some miracle, it goes in.  If I were half as good at making that type of shot, my childhood NBA dreams probably would have come true.

    Yet, as fans, we all love Marion.  Despite a decline in production, he can still nail some electrifying three-pointers and throw down some amazing dunks.  The best part is that his passion for the game is still there, and it shows.  Other players with such a decline probably would have mentally checked out long ago.

Avery Johnson

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    As a coach, Avery Johnson is the basketball equivalent of former New York Jets coach Herman Edwards.  He speaks what's on his mind and tells it like it is.

    Call me brash, but I think that's incredible.  Not only does it give the fans a laugh, but coaches even doing that today is a rarity.  Too many hold back and PC the press conferences up and thus, it can be hard for some people to respect them.

    Johnson wears his passion for the game and for coaching on his sleeve and while it should be taken seriously, it's funny as hell in some instances.

Dan Gilbert

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    Like David Kahn, Cleveland Cavaliers owner Dan Gilbert is entertaining in the fact that he just doesn't care.  After LeBron James flipped off the Cleveland fans and took off for Miami, Gilbert showed off his guts and wrote an open letter to said fans.  This letter made a daring proclamation that the Cavs would win a title before James won a ring with the Heat.

    It doesn't matter whether or not Gilbert will turn out to be right or wrong.  The fact that he called out his former star player on that level is just incredible.  Who knows how he'll react if Kyrie Irving demands a trade?

Walt "Clyde" Frazier

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    Just look at that suit, folks.  That's former Knicks point guard Walt "Clyde" Frazier as one of the O.G.'s of basketball.  He continues that tradition today, wearing even crazier suits.

    On top of that, the ridiculous phrases he uses make watching a Knicks game an experience, and a damn good one.

Scot Pollard

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    Ladies and gentlemen, may I present to you: the many hilarious hairdos of Scot Pollard!

Chris Andersen

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    This may be a rhetorical question, but how can anyone not be entertained by this guy?  The fact that he has that much ink covering his body and opposing players keep a straight face around him is astounding.

    Love him or hate him, the Birdman and his body ink are entertaining.  Heck, I laugh every time I see those crazy tattoos.

Larry Johnson

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    If you were a kid in the '90s who loved basketball, you definitely remember this commercial.  In less than 30 seconds, Larry Johnson went from being an awesome forward for the Charlotte Hornets to a subject of humorous remarks.

    A true pro, the man notoriously dubbed "Grandmama" embraced it and continued to do his job on the hardwood.  Throw in his famous post-shot gesture, and Johnson was simply the man.  The commercial only further proves so.

Yao Ming

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    When Yao Ming was drafted, NBA fans went into a frenzy.  Here was someone who could be the next big international star, so of course he was going to be hounded by both fans and the press.

    The man took it all like a champ and made the most of a career that was tragically cut short by injuries.  The best part about it all is that during that time, Yao had no problem making fun of himself and his adjustment to a new league.

    Watch the commercial at the left and you'll see some classic Yao gold.

Jalen Rose

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    From being a member of Michigan's Fab Five to a decent shooter for 13 NBA seasons, Jalen Rose has made the most of his time as an ESPN analyst.  Whenever he's on, he provides great insight combined with excellent humor.

    Simply put, the man has swagger.  Nothing can get him down.  His loud style matches perfectly with fellow analysts like Ric Bucher and, unlike other analysts, he is not afraid to tell it like it is.

    Just watching him can be a riot sometimes, a rare case considering most sports news shows.

Allen Iverson

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    In all honesty, it's hard not to laugh at a player as cocky as Allen Iverson.  The man was talented, but his off-court antics and drama tended to generate more press than the work he did on the court.

    His most infamous (and most entertaining) moment came in 2002, when his Philadelphia 76ers were eliminated in the first round of the playoffs.  Then-coach Larry Brown cited Iverson's missing team practices as the reason the team did so badly, and Iverson went on a legendary rant.

    If you don't laugh at the video, clearly I have not done my job.

Vince Carter

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    When I was a kid, the one thing I wanted to do the most was dunk a basketball on my own.  When the cruel mistress known as genetics robbed me of that athleticism, I turned my attentions to Vince Carter.

    Simply put, this man took the art of dunking to a whole new level.  Every slam he threw down was with authority times 100.  If it were a street game, he would do the following: dunk on you, do the Mutombo finger wag and drink all of your Gatorade before leaving the playground with your girlfriend.

    That kind of confidence is seen in the NBA today, but not in the same way Carter brought it to the table.  The image of "Vinsanity" has faded over time, but an extra shot of it could be just what is needed for Carter to save his career.

    Still, in his prime he was one of the most entertaining not just in basketball, but in all sports.

Rasheed Wallace

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    When Rasheed Wallace was with the Portland Trail Blazers, my friends and I would make one particular wager on a regular basis.  The terms were simple: Guess whether or not the man would get kicked out of the game, then make a bet on when in the game it would happen.

    Don't get me wrong, the man was talented.  Still, despite posting respectable career averages of 14.6 points and 6.7 rebounds, Wallace will always be known for his undeniable skills at receiving technical fouls.  As much as I hate to say it, his volatility was surely the only reason some of us East Coast kids stayed up to watch the West Coast games.

Marv Albert

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    This may sound far-fetched, but Marv Albert is one of the greatest (if not the greatest) broadcasters in basketball history.  Some of us grew up with him on a regular basis, while others just heard him work national games of the week.

    No matter how you look at it, the man is fun to listen to.  His exuberant cries of "YES!" following a clutch shot are some of the most recognizable calls of all time, and the man is an icon of the sport.

Gus Johnson

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    In keeping with the broadcaster theme, let's talk about Gus Johnson.  Sure, he's primarily known for his work during the NCAA tournament, but he's got an impressive NBA resume as well.

    The always-excited Johnson was the Knicks' radio voice for years, calling Allan Houston's famous playoff shot against the Miami Heat and even working some games on TV.

    Love him or hate him, the man's style is fun and really gets you into the game even if you don't care about the teams involved.

World B. Free

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    Forget the fact that he averaged 20.3 points a game for his career.  Lloyd Bernard Free makes this list simply because he made one of the most hilarious decisions in basketball history.  In 1981, he had his first name legally changed to World.

    This combined with his skill on the court make Free one of the NBA's most entertaining individuals.  This honestly could be better than another name change we'll get to later.

Isiah Thomas

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    I'll leave out everything about the man's messy tenure with the New York Knicks, as none of that was entertaining at all.  Rather, Thomas was one of the game's most entertaining players when playing for the Detroit Pistons on the legendary "Bad Boys" teams.

    The teams that Thomas played on in the '80s exemplified blue-collar play, one full of toughness and tactics that some considered dirty.  The man known as "Zeke" was no exception, as his tough defense ticked a lot of people off and his clutch shooting frustrated opposing fans and teams.

    Even in retirement, Thomas showcased the same cockiness he did on the court as a player.  To date, he appears to have no remorse for running the Knicks into the ground.  Man, and I thought LeBron was cocky...

James Dolan

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    Forget the larger-than-life ego.  Forget the horrific front office decisions to which he has contributed.  The one reason why Knicks principal owner James Dolan is entertaining is within the video to the left.

    A word of advice: The key to enjoying the video is to not take it seriously, just like how the man hasn't taken running the Knicks as seriously.

Pat Riley

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    The entertaining aspect of Pat Riley is, of course, his cockiness.  Here is a man who, at the start of the 2005-2006 season, supposedly forced the resignation of then-Miami Heat coach Stan Van Gundy and took over before ending the season with an NBA Finals victory.

    On top of that, just look at the man.  Is he running a basketball team or a casino?  That image just screams someone who knows how to entertain.

    Throw in the fact that he's done some commercials in his lifetime, and the entertainment resume just gets longer.

Tree Rollins

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    Many of you have probably never heard of Tree Rollins.  He spent 18 years in the NBA, mostly with the Atlanta Hawks and made a name for himself as a shot blocker.

    Yet, everyone seems to remember Rollins for one particular incident that occurred in a 1983 playoff game against the Boston Celtics.  While running up the court, Rollins took a swing at Celtics guard Danny Ainge.  In return, Ainge tried to tackle Rollins and both fell to the floor before a skirmish ensued.  The funny part is Ainge's claim that Rollins bit him.

    OK, I've heard of a lot of things happening in on-court fights: shoving, punching, head-butting, etc.—but biting?  Where did Rollins get that idea?  I'm sorry, but that's just hilarious of him to even do, considering his considerable size advantage over Ainge.

    Thus, albeit just for one incident, Rollins makes the entertaining list.

Bill Walton

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    In terms of broadcasting, you've got to love Bill Walton.  A seasoned NBA veteran, his insight is always welcome as is his passion.

    Yet, and I'm prepared for the hate mail over this, Walton is just fun in the fact that his voice is kind of funny.  Listen to him in the clip at the left.  The man legitimately sounds as though he's got a few marbles in his mouth.

    On top of that, it's hilarious how excited he gets over a member of The Grateful Dead being at the game.

Stephon Marbury

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    As a Knicks fan, I'm inclined to hate Stephon Marbury with a passion.  Yet, I've got to give the man credit.  When he was in his prime and not pissing the rest of his teammates off, he was a good player and entertaining to watch.

    Yet, the highlight of Marbury being entertaining came a couple of years back.  He posted a famous video of himself, claiming that Vaseline was a good home remedy for a sore throat.  Marbury then proceeded to eat the Vaseline.

    This now poses the question: Could eating Vaseline be the reason Marbury was so hard to deal with?  Something tells me it may have some negative side effects if ingested.

Reggie Miller

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    Love him or hate him, Reggie Miller was easily the best and most entertaining trash-talker of his generation.  The even better part was that he could back it up.

    He would trash-talk a defender into getting distracted, sink a clutch three-pointer and then talk even more trash.  His most legendary incident of this came during the 1994 Eastern Conference Finals against the New York Knicks.  In a game that his Indiana Pacers won, Miller famously got into an argument with longtime Knicks fan and veteran filmmaker Spike Lee.

    As a fan, I should be siding with Spike.  Yet, I'll be the first to admit that their argument was drop-dead hysterical and wildly entertaining.

Karl Malone

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    A wise man once said that imitation is the sincerest form of flattery.  If that is indeed true, the poster child of that saying could be Hall of Famer Karl Malone.  "The Mailman," besides being a phenomenal dunker and forward, was one of the most brutally honest players in the history of the game, making his staunchly conservative political views known by appearing in ads for the NRA and not apologizing for them.

    How did his views make him entertaining?  Well, his thick Louisiana accent just made Malone a fun guy to listen to speak.  On top of that, he's frequently impersonated by Jimmy Kimmel.  If that's not the sign of an entertaining player, I don't know what is.

Kevin Garnett

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    Though some may consider him to be arrogant and over the hill, Kevin Garnett's trash-talk is what makes him entertaining.  He knows that he's not the dominant forward he used to be and he flat-out doesn't care.

    This man will say what he wants when he wants to and won't back down, except when it involves saying that Charlie Villanueva is a cancer patient.  To some, he's a punk and a coward.  To me, though I hate the team he plays for, he's one of the game's most entertaining personalities and players.

Phil Jackson

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    Phil Jackson is easily the best coach in NBA history.  He has won 11 championships in coaching stints with the Chicago Bulls and Los Angeles Lakers and helped launch the careers of big names like Kobe Bryant and, of course, Michael Jordan.

    Yet, one thing you'll notice about Jackson is that he rarely ever gets flustered when being interviewed, particularly after a bad game.  The man known as "The Zen Master" is a practicing Buddhist and has let his inner calmness create some of the funniest sideline moments in basketball history.

Dennis Rodman

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    Be it appearing in drag, head-butting a ref or kicking a cameraman, there's no denying Dennis Rodman was a riot in the prime of his career.  The man was a phenomenal rebounder, but his crazy hair tended to outshine his skills on the court.

    On top of that, Rodman showcased his talent off the court by appearing in bad action films like Simon Sez and Double Team.  The fact that his already over-the-top personality tried to make it in movies is just drop-dead funny to me.

    He's now a Hall of Famer and seems to have toned down his act a bit, but fans of my generation will always remember Rodman as the entertaining heel with the wild hair.

Julius Erving

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    Julius Erving was a flashy player who got his start in the ABA before coming to the NBA.  In the former league, he gained a reputation as an incredible scorer and rebounder.  Yet, once the leagues merged and Erving became part of the Philadelphia 76ers, he brought with his electrifying personality something even better: the tomahawk dunk.

    The fact is that Erving was one of the NBA's first true dunkers.  Fans had never seen much of this before and were instantly entranced.  Throw in his constant game-face, and this is a man who was truly fun to watch.

Mark Cuban

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    Hypothetically speaking, let's say Spike Lee one day decided to buy the New York Knicks.  Sure enough, he would be in his same courtside seat every home game (Lee is too cool for the owner's box) and be his same excited self.  With every clutch dunk or three-pointer, he would jump up and down and cheer loudly.

    In doing that, Lee would be the Eastern Conference equivalent of Mark Cuban.  This man puts to rest the stereotype that all team owners are these crusty and overly professional old men in suits and is easily one of the NBA's greatest fans.

    I'm going to go out on a limb right now and say that if a majority of the owners of the teams in the NBA were more like Cuban, we wouldn't be having a labor dispute right now.  Never before have I seen someone so devoted to their team and willing to do anything to win, even if it means criticizing refs and getting fined on occasion.

    The fact is that Cuban has changed the way owners are depicted in the sport, and I'm OK with that.  His passion and excitement is a breath of fresh air compared to some owners, who barely have any involvement with their teams at all.

Wilt Chamberlain

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    Seriously, what's not to like about Wilt Chamberlain?  The man holds the record for most points scored in a single game with 100 and is considered to be the first dominating center in the history of the game, along with Bill Russell.

    Yet, what made Chamberlain entertaining was his swagger.  This guy told the world, with a straight face no less, that he had slept with more than 20,000 women.  I have one thing to say to that: yowza!

    If this claim is indeed true, the fact that Chamberlain still had enough strength to stand up and say it is astounding.  Throw in the charisma he had as a player, and he is definitely one of the game's most entertaining people.

Charles Barkley

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    I loved him as a player, but I easily love Charles Barkley more as a broadcaster.  The Round Mound of Rebound has no filter, even when he's on national television.  He has his opinions and he states them no matter how controversial or outlandish they may be.

    If you're watching him on TV at home with some buddies, you could easily play a game called "What's Charles Going to Say Next?"  Heck, make some bets on it!

    Some may find him a bit too out there, but that's besides the point.  The fact is Barkley was once an expert at keeping fans in the seats as a player and now he's doing an even better job keeping the fans at home watching him on their TV sets.

Shaquille O'Neal

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    No matter what team you root for, don't look anybody in the eye and tell them you don't like Shaq.  This guy is an NBA icon both on and off the court, be it stuffing a dunk down someone's throat or having some hilarious banter with the press.

    The fact is that Shaq knew how to balance out work and fun almost perfectly and in the process became a complete and utter goofball.  I mean, come on.  Why else would he make movies like Kazaam and Steel?

    Oh, and let's not forget that he contributed to one of the most awesome rap songs of all time and gave us a rap that we'll never forget.  Even though he was nowhere near as good in the twilight of his career, I must say I'll miss the man's antics.  Yet, he'll have a chance to continue what he started as a player as he makes the transition to analyst when he joins Charles Barkley on TNT.

Ron Artest/Metta World Peace

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    Ron Artest/Metta World Peace is one of those players who is entertaining simply because you never know what to expect from him.  One day, he may be thanking his psychiatrist on national television.  On another, he'll be appearing on Jimmy Kimmel Live in his underwear.

    His unpredictability is almost at the point where we can forgive him for the infamous Malice at the Palace, but he's still got a ways to go from that.

Kobe Bryant

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    Kobe Bryant is a player who some people hate with a passion and I wish I knew why.  He seems like a well-rounded individual and his teammates love him, with the exception of Shaq.

    More importantly, he understands the power of building his brand and as exhibited by the commercial to the left, his sense of humor is pretty good as well.  For him, it's all about winning and reaching out to the fans.  On top of all that, the man is just plain fun to watch.

LeBron James

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    Love him or hate him, you cannot deny that LeBron James is one of the most entertaining players in basketball.  He has a large ego, but puts it to use when he (at least sometimes) demands the ball late in games and takes crazy shots.

    Yet, the larger part of James' entertaining personality comes in his desire to put his face out there regardless of circumstance.  From "The Decision" to the hilarious "Most Valuable Puppets" commercials that featured puppet versions of himself and Kobe Bryant as roommates, there doesn't seem to be anything the man won't do to please the fans.

Dirk Nowitzki

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    Once again, we come to a slide where my words cannot do the man justice.  Watch the video.

Dwight Howard

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    On the court, Dwight Howard is a lean, mean, scoring and rebounding machine.  His dunks bring down the house and his stoic demeanor following them just fires up the fans more.

    Yet, off the court, Howard is a complete and utter goof and that's why some fans adore him even more.  The fact that he has no problem acting like a dork in certain commercials speaks volumes about him and believe it or not, it makes it hurt a little less whenever the Magic beat the Knicks.

    Hopefully, once Howard makes a free-agency decision, it will bring about more funny commercials as well as some funny moments on the court.

Michael Jordan

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    Come on, people.  You really think we would have a slideshow about the most entertaining personalities in basketball history and not include His Airness?  To leave him out would be a crime.

    The fact of the matter is that whether you loved the Chicago Bulls or not back in the '90s, you couldn't help but love Michael Jordan.  From his famous tongue antics to his unbelievable shooting touch, it was impossible to hate the man.  On top of that, he was completely humble despite being the best.

    Yet, what makes Jordan one of the most entertaining people in basketball history (if not the most) is the fact that he was able to let his hair (or lack thereof) down and do a ridiculous kids movie in Space Jam.  Say what you want about the movie, but there's something hilarious about MJ running up and down the court with Bugs Bunny and Daffy Duck as they play a game against evil aliens.