Will Smith’s Most Unprofessional and ‘Immature’ Moment Involved a Same-Sex Kiss

Willard Carroll Smith Jr. — simply known as Will Smith, or the Fresh Prince to some — is one of the biggest actors in Hollywood. From his start in NBC‘s The Fresh Prince of Bel-Air to his more recent films, such as Netflix‘s Bright, Smith has become known for his method acting, extensive range, and his numerous awards (including two Academy Awards and five Golden Globes).

But despite his expansive repertoire, there is one stand-out moment in his acting past that he says was “immature.” To paraphrase the iconic lyrics of the Fresh Prince himself: Now, this is a story all about how Smith’s acting got flipped-turned upside down. And we’d like to take a minute, just sit right there. And we’ll tell you how he didn’t want to kiss a man over there.

Will Smith got his fresh start in the ’80s and ’90s

Will Smith
Will Smith | Getty Images

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Before he was shooting aliens out of the sky in 1996’s Independence Day, and before he was evading detection in the spy thriller Enemy of the State, Smith was known as the Fresh Prince.

Along with his friend DJ Jazzy Jeff, the duo went on to win a Grammy for their song “Parents Just Don’t Understand.”

With his popularity growing, Smith leveraged his popularity and signed on with NBC to create a sitcom entitled The Fresh Prince of Bel-Air. The sitcom aired for six seasons, and was a rating smash (it’s also slated to be rebooted and released in 2021 by HBO Max). 

But Smith didn’t want to just stick with being a sitcom star. According to a 2007 issue of Time magazine, Smith declared back in the 1990s that, “I want to be the biggest movie star in the world.”

And he got his chance when he was cast in the movie Six Degrees of Separation.

‘Six Degrees of Separation’ was Will Smith’s big break

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Six Degrees of Separation was a comedy-drama released in 1993. In it, Smith plays the role of Paul Poitier, a young man who has recently arrived in New York City.

The movie’s escapades kick-off when Poitier shows up at the home of two of a rich couple (played by Stockard Channing and Donald Sutherland). 

Poitier tells the couple that he is best friends with the couple’s children (even though he is not), and he begins to con them into giving him access to their upper-class, elite lifestyle.

The film was nominated for numerous awards, and the critics at Rotten Tomatoes attribute much of the film’s success to Will Smith’s acting.

But there was one specific scene in Six Degrees of Separation that Smith simply couldn’t act his way through, and he spoke about it with regret in an old interview with Entertainment Weekly.

Will Smith says he was “immature” about a same-sex kissing moment

Will Smith at the European premiere of 'Suicide Squad'
Will Smith at the European premiere of ‘Suicide Squad’ | Anthony Harvey/Getty Images

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Anthony Michael Hall is the actor who plays Trent Conway, a gay man in Six Degrees of Separation who helps to teach Smith’s character how to be a conman. In a 1998 chat on AOL, Hall said that the role was one of the “hardest” that he’d ever done at that point in his career.

But he wasn’t the only one having difficulty during some of the film’s scenes.

In the movie, there is one point where Smith as Poitier is supposed to kiss the Conway character. It looks like they do, but in reality, it was a bit of movie editing magic. In fact, the scene cuts in such a way as to imply that Smith had kissed another man, but it didn’t actually occur. 

In an interview with Entertainment Weekly back in the early 1990s, Smith said he thought he could do it, but he changed his mind about the same-sex makeout session at the very last minute. The reason he cited was that was worried what his friends back home would think (after all, he was still best known as the rapper Fresh Prince). 

However, the scene was pivotal for the movie, so the director ended up filming the actors’ heads from behind. Then, the director had to use body doubles to make the kiss happen. 

“It was very immature on my part,” Smith told Entertainment Weekly. ”I was thinking, ‘How are my friends in Philly going to think about this?’ I wasn’t emotionally stable enough to artistically commit to that aspect of the film. In a movie with actors and a director and writer of this caliber, for me to be the one bringing something cheesy to it.”

“This was a valuable lesson for me,” he said. “Either you do it or you don’t.”