It’s safe to assume that Will Smith is one of the most famous Hollywood celebrities in the world. Indeed, Will has truly done it all in Hollywood. In the 80s, he exploded onto the scene as a rising rapper. Later, he became a television star before becoming a major movie star.
Will has starred in Oscar-nominated movies and classic summer blockbusters. His marriage and family often garner a great deal of media attention. Of course, Will’s career has its peaks and valleys. There were times when he chose just the right projects and was on a hot streak.
However, Will Smith is a very open and honest person. He admits that he has made a few mistakes in his career and life. Of course, Will does his best to learn from them. Regardless, he does have a few regrets and realizes he made some questionable choices. It’s not just his career that gives Will regrets. He would also change the way he handled situations with his wife and kids.
It’s time to take a closer look at Will Smith’s career and life. Here are a 13 Things Will Smith Admitted He Regrets Today.
13 Regrets Making Wild Wild West
In the late 90s, Will Smith was box office magic. Indeed, he was on a hot streak and starred in several major hits, such as Bad Boys, Independence Day, and Men In Black. Everything he touched turned to gold - and he knew it. However, that all come crashing down.
In 1999, Will portrayed Captain James T. West in Wild Wild West. It’s one of the most expensive movies ever made and ended up being a box office bomb. It was also one of the worst movies of the year. Smith openly admits that he made a mistake by agreeing to star in Wild Wild West. If he could go back in time, he would make a different choice.
Related: 16 Facts About Will Smith That Leave Us Scratching Our Heads (But Are Hard To Ignore)
12 Regrets Vlogging Surgery
In late 2019, Will Smith underwent a colonoscopy and decided to document it. Indeed, Will filmed himself before the procedure and right after. He ended up posting the 17-minute video as a joke but realized it bombed. Later, Will admitted that he regrets sharing the video.
Will noted, “I was doin’ it as a joke. I thought it was gonna be funny. Yeah, it turned out not to be really funny.” Will learned from his mistake and promised not to make it again. He added, “Do not vlog your colonoscopy. Note to self.”
11 Regrets Financial Trouble In The 90s
In the late 80s, Will Smith had his first big break as part of the rap duo, DJ Jazzy Jeff and The Fresh Prince. They released several hits, including “Parent’s Just Don’t Understand.” They even won the first Grammy Award for Best Rap Album in 1989. However, Will didn’t do a good job saving his money and was broke by the early 90s. He learned a harsh lesson as he had to deal with the IRS.
Will realized wasting all his money was a significant mistake. Will turned things around when he starred in the hit NBC series, The Fresh Prince of Bel-Air. He soon became one of the wealthiest celebs in the industry.
10 Regrets Backlash Against Jaden’s Career
Will Smith and his wife, Jada Pinkett Smith, attempt to give every opportunity to their kids that they can. Indeed, Jaden Smith and Willow Smith are making a name for themselves in the industry. However, Jaden has received significant backlash. Will realizes that part of that is because of his help.
Will did everything he could to launch Jaden’s acting career, but it backfired. Instead of continuing the family legacy, Will was accused of nepotism because many critics felt Jaden wasn’t up to the standard. Jaden’s acting career has stalled while he focuses on other aspects of life.
9 Regrets Encouraging Children’s Artistic Freedom And Relaxed Parenting Rules
Will Smith and Jada Pinkett Smith have always had unique parenting techniques. Indeed, they don’t believe in punishing their kids. These kids were raised with very relaxed parenting rules. However, Will now regrets some of his parenting methods, such as encouraging artistic freedom.
Jaden and Willow Smith often stir up a ton of controversy. Willow posed provocatively at the age of 13, in a picture with a much older man. Also, Jaden makes wild comments that make him seem out of touch with reality. Will said about his parenting techniques, “Yeah, I think that might have been a mistake. We may have gone too far.”
Related: 20 Rules Will Smith And Jada Make Their Kids Follow
8 Regrets Tricking Fans To See Movies
As noted, Will Smith considers Wild Wild West one of his biggest movie regrets. However, there are many aspects of the movie that Will regrets. For instance, Will feels he tricked his fans into seeing the movie. Will was so focused on making another blockbuster movie that he didn’t care about the quality of the film. Will regrets doing that to his fans.
Will noted, “My career has been strictly being able to sell my products globally, and now it’s in the hands of fans. I have to be in tune with their needs and not trick them into going to see Wild Wild West.”
7 Regrets 90s Fashion Choices
Willow and Jaden Smith both have their own unique fashion sense. Indeed, Jaden has dressed in female clothing on a few occasions. At first, Will questioned his kid’s fashion sense. Well, until they found a picture of their dad from his younger days.
During an episode of The Fresh-Prince of Bel-Air, Will wore a crop top, which showed off his midsection. Will regrets bringing up style to his children. Will posted a pic and noted, “This is the picture my kids showed me the last time I commented on their fashion. Haha. Last time I do that.”
6 Regrets After Earth
In 2013, Will and Jaden Smith starred in M. Night Shyamalan’s After Earth. Will thought the movie would do well and was an excellent way to elevate Jaden’s career. However, the film bombed at the box office and Jaden received some brutal backlash. Will was devastated that the film failed but also hated dragging Jaden into it.
Will admits that the film is one of his “most painful failures.” After some deep reflection, Will realized that topping the charts isn’t the most crucial thing in the world.
5 Regrets Wanting To Be The Biggest Movie Star In The World
In the 90s, Will Smith was on a hot streak. He starred in a string of box office hits and topped the music charts. However, the streak ended with Wild Wild West. At the time, Will focused his attention on becoming the biggest movie star in the world. He had lost sight of the passion that brought him to that point. He cared most about being a success at the box office and getting a big check.
Will said, “I wanted to win and be the biggest movie star, and what happened was there was a lag - around Wild Wild West time, and I found myself promoting something because I wanted to win versus promoting something because I believed in it.”
4 Regrets Being Jealous Of Jada Pinkett Smith’s Friendship With 2Pac
The late Tupac Shakur is considered one of the greatest rappers of all time. In the 90s, Will Smith topped the rap charts with his family-friendly hip-hop. However, Tupac also became a household name, with a more gritty and violent style of rap. Regardless, both were poetic in their own way.
Will met and fell in love with Jada Pinkett in the early 90s. Jada and Tupac were childhood friends that had a very close bond. Will admits that he was jealous of the friendship and was not kind to Tupac. Will admits he wishes he handled it better and said, “That was a big regret for me, too, because I could never open up to interact with Pac.”
Related: Jada Pinkett Smith’s Friendship With Tupac Made Will Jealous
3 Regrets Men In Black II
In 1997, Will Smith starred in the summer blockbuster, Men In Black, along with Tommy Lee Jones. Will was on a roll, and every summer, he was the talk of Tinseltown. For the most part, Will stays away from sequels. Indeed, he’s starred in several movies that fans hoped would have sequels. However, there’s one sequel that Will regrets to this day.
In 2002, Will starred in Men In Black II, which didn’t achieve the same level of success. His hot streak was already over, but this sequel didn’t help. Will admits he wasn’t pleased, “I had fumbled a few of my last sequels, you know? I wasn’t happy with the Men In Black sequel.” Regardless, Will returned to the role a third time in 2012, for Men In Black III.
2 Regrets Rocky Relationship With Eldest Son, Trey
Will Smith’s eldest son, Trey, isn’t in the spotlight like his half-siblings, Jaden and Willow. In the early 90s, Will was married to Trey’s Mother, Sheree Fletcher. However, the relationship didn’t work and they divorced. It put a strain on his relationship with Trey, and they weren’t always close to each other.
Will regretted the distant relationship with his son and made up for it. Will opened up about their problems on Twitter, “We struggled for years after my divorce from his Mother. He felt betrayed & abandoned. It is a wild blessing to recover & restore a loving relationship with my son.”
1 Regrets Turning Down The Matrix
Will Smith has turned down many roles in his career. However, there is one role that he regrets turning down, and it still haunts him to this day. Indeed, Will was offered the starring role as Neo in the critically and commercially-acclaimed classic, The Matrix. The groundbreaking film went on to change movies forever.
However, Will didn’t get the concept of the movie and passed. Instead, he chose to star in Wild Wild West, which flopped and made him feel worse. Indeed, if Will could go back, he’d tell young Will to make a different choice. Will said, “I’d go back to Wild Wild West, and I would say, ‘(expletive), why didn’t you do The Matrix?’”
Next: 10 Roles Will Smith Turned Down (And 5 He Was Rejected For)
