The Shady Side Of Will Smith

Will Smith has come a long way since he left Philadelphia, where he was born and raised. But he was a popular guy even before he and DJ Jazzy Jeff appealed to an entire generation of aggrieved teens with their 1988 Grammy-winning song, "Parents Just Don't Understand." Smith's high school classmates gave him the nickname Prince Charming, per Britannica, and this inspired his stage name: Fresh Prince.

But while Smith's magnetic personality helped make him a star early in life, his behavior wasn't always princely. In an episode of his YouTube series "Storytime," Smith recalled how he tried to make an impression on everyone at a new school by strutting into the lunchroom and announcing, "Can I have y'all attention, please? He's here." No one was impressed, and one student told him, "Man, don't nobody give a f*** that you're here." Smith shot back, "Just give me 10 minutes. Your girl gonna care."

Smith made an instant enemy who later got revenge by sliding the shackle of a combination lock over one finger and punching Smith in the face. The rapper regretted his actions after he saw his attacker being led away in handcuffs, saying, "I had the recognition that I had caused this kid to throw his life away." He also made a promise to himself that he would only act in a manner that would set a good example for others — but this is a story all about how the Fresh Prince hasn't exactly lived up to his vow.

The Fresh Prince paid the price for ignoring the IRS

Early in his career, Will Smith made the same mistake as so many young celebrities who end up broke: He assumed that cash would keep flowing in after he got his first taste of fame. "Before I was getting in trouble with Uncle Phil, I was in trouble with Uncle Sam," "The Fresh Prince of Bel-Air" star said in an episode of "Storytime."

As part of the hip-hop duo DJ Jazzy Jeff & the Fresh Prince, Smith released a successful album titled "He's The D.J., I'm The Rapper" and won a Grammy in 1988. He then went on a spending spree, buying designer clothing, cars, and motorcycles. But the rapper made another huge financial error: He didn't pay his taxes. To make matters worse, sales of his second album were dismal, so the then-19-year-old had no money to pay the U.S. government when it noticed his neglect. "The IRS came and took all my stuff," Smith recalled on "60 Minutes" in 2007. He estimated that he owed about $2.8 million in back taxes and had less than $5 in his bank account.

After losing pretty much everything, Smith decided to move to Los Angeles. "So I borrowed $10k from a friend of mine who was a purveyor of neighborhood pharmaceuticals," he told actor Idris Elba while promoting his memoir "Will" at the Savoy Theatre in London, per Metro.

Why Will Smith wouldn't talk to Tupac

So many of Will Smith's contemporaries would have clamored for the opportunity to speak to Tupac Shakur, but a green-eyed monster kept the "Men in Black" star from showing the "California Love" hitmaker any love. Shakur was close friends with Will's wife, Jada Pinkett Smith. She even possesses at least one unreleased poem by the late rapper, which she shared on Instagram in 2021.

During a 2020 appearance on "The Breakfast Club," Will spoke about Jada's bond with the man he once viewed as a rival. "They grew up together ... [Jada] just loved him. He was the image of perfection, but she was with the Fresh Prince," he said. Jada begged Will to get to know Shakur, believing that the two would become friends if Will would just break the ice. But even when Will found himself in the same room as Shakur, he steered clear of him. "I suffered a raging jealousy: I wanted Jada to look at me like that," Will confessed in his autobiography. "The way Jada loved 'Pac rendered me incapable of being friends with him. I was too immature."

Shakur was shot and killed in 1996, and by 1998, Will had recovered from his jealousy enough to pay tribute to Shakur while accepting his Grammy for best rap solo performance. During his "Breakfast Club" interview, Will confessed that he now wishes he'd put his pride aside and spoke to Shakur when he was alive.

He was investigated by the Department of Children and Family Services

Will and Jada Pinkett Smith have confessed to using some unconventional parenting methods to raise their kids, including being lax with rules and discipline. "Our concept is, as young as possible, give them as much control over their lives as possible," Will told Metro in 2013 (via E!). But some critics seemingly thought the parents were being far too permissive in 2014 when 20-year-old actor Moises Arias shared an Instagram photo of their then-13-year-old daughter, Willow Smith, lying on a bed with him.

Per TMZ, Arias deleted the pic, but not before someone decided that it merited an investigation. The Los Angeles County Department of Children and Family Services eventually cleared Willow's parents of any wrongdoing, with an insider telling Radar that there was "no evidence presented that Willow has ever been in any danger around Moises, or that she has ever been physically or emotionally abused." However, Will and Jada were reportedly told to monitor their kids' social media accounts a little more closely.

Jada and Willow spoke about the incident during a 2019 "Red Table Talk" episode. They revealed that the person who contacted authorities had claimed that Will and Jada were starving Willow, who decided to eat a bowl of cereal in front of a visiting social worker to disprove the allegation. "The kids got to see for the first time why Will and I had been so protective," Jada said of the ordeal. 

The actor's homophobic behavior

As "Old Town Road" hitmaker Lil Nas X can attest, homophobia is still an issue in the hip-hop industry, but some Will Smith fans might be surprised to learn that the "Wild Wild West" rapper — who makes it a point to keep his lyrics rated PG — is guilty of making ugly, prejudiced remarks about gay people.

According to the Advocate, the 1986 album "He's The DJ, I'm The Rapper" features a recording of Smith telling a live audience, "All the homeboys that got AIDS be quiet / all the girls out there that don't like guys be quiet." And this wouldn't be the only time he would insult the gay community. In the midst of filming "The Fresh Prince of Bel-Air," Smith decided to prove that he was ready for serious movie roles by starring in the 1993 film "Six Degrees of Separation." But what he wasn't ready for was a scene that called for him to kiss co-star Anthony Michael Hall. "I was thinking, 'How are my friends in Philly going to think about this?'" Smith said in a 1993 Entertainment Weekly interview. "I wasn't emotionally stable enough to artistically commit to that aspect of the film."

Smith's explanation didn't fly with actor Ian McKellen, who wrote on his website, "[Will's] twinge of homophobia was unseemly and unnecessary. When I met him at the Los Angeles opening of the movie, I made sure to give him a kiss for the benefit of the paparazzi."

Why Big Willie has a mugshot

Will Smith chased down bad guys in the 1995 buddy cop movie "Bad Boys," but years earlier, he found himself on the wrong side of the law. Smith got arrested in 1989, so he had some real-life experience to draw from when he was shooting his mugshot scene in "Hancock."

In 2012, the National Enquirer published Smith's mugshot photos and listed his charges, which included assault. His bodyguard had beat up a record promoter and severely injured one of his eyes, allegedly at Smith's behest. In his memoir "Will," Smith explained that he was only arrested due to the existence of a Pennsylvania law stating "that if one person commits a crime under the control or direct influence of a master, then the 'master' is legally liable for the actions of the submissive/slave party." He also accused the victim's attorneys of pursuing legal action against him because they assumed that they could get a big payout. But, he wrote, "The joke was on them. I didn't have a dime to my name."

The charges were dropped, but Smith had to stay in jail longer than he should have because his arrest happened on a Friday. Spending the weekend in the clink gave him plenty of time to think. "I am laying on the floor in a jail cell and I am like, 'You've got to be kidding me!'" he said on "The Oprah Conversation." "I won a Grammy eight months ago. Like, what is happening?"

The married actor confessed to falling in love with a co-star

It's not unusual for actors to fall for their co-stars, but when a marriage is involved, things can get messy. Will Smith was married to his first wife, Sheree Zampino, when he landed a role in the 1993 movie "Six Degrees of Separation." The young actor was filming with a cast of seasoned thespians that included Donald Sutherland, Ian McKellen, and Stockard Channing, and naturally, he wanted to prove himself worthy of working with them. Unfortunately, an experiment with method acting made his personal life awkward.

"Sheree and I were in the first few months of our marriage with a brand-new baby and for Sheree, I can imagine that this experience was unsettling to say the least," Smith wrote in his autobiography (via Vanity Fair). He eventually realized that he'd gone overboard with his attempts to stay in character at home. "My character was in love with Stockard Channing's character. And I actually fell in love with Stockard Channing," Smith confessed to Esquire. "So the movie was over and I went home, and I was dying to see Stockard. I was like, "Oh no! What have I done?" He did eventually see his co-star, but decided to keep his crush to himself. 

When the "Grease" star learned about Smith's feelings for her many years later, she had nothing but praise for her secret admirer. "That's very lovely to hear," Channing told GQ. "We liked each other and trusted each other. That's actually quite rare."

He was still married when he started dating Jada Pinkett Smith

Will Smith was already interested in Jada Pinkett Smith when he met his first wife, "The Real Housewives of Beverly Hills" star Sheree Zampino. In a 2018 "Red Table Talk" episode, Will recalled seeing Jada on an episode of "A Different World" and feeling an instant attraction to her.  He attended a taping of the sitcom in hopes of meeting her, but Zampino caught his eye while he was there, and they ended up clicking. 

Will and Zampino ended their three-year marriage in 1995. By then, Will had met Jada, and while Jada is adamant that Will did not cheat on Zampino with her, Will recalled how his feelings for Jada overwhelmed him when he was out with his wife one night. "I had to get up from dinner when I had a realization that I wasn't with the person I was supposed to be with," he confessed. 

Zampino is actually the one who decided to file for divorce. "[Will] didn't have the capacity to give me what I needed," she explained on "Hollywood Unlocked." But it still stung when Will started dating Jada before their divorce was finalized. On "Red Table Talk," Zampino spoke to Jada about one of the fiery exchanges they had at the time. "[I said], 'B***h, you living in the house I picked out!' And you said, "It's my house now," Zampino recalled. Fortunately, the women were able to look back on the incident and laugh. 

Will Smith wanted a harem of 20 women

Will Smith's songs might be squeaky clean, but the "Gettin' Jiggy Wit It" singer seems to have a hard time censoring himself when it comes to his sex life. After getting in peak physical condition to play boxer Muhammad Ali in 2001, he told Premiere (via Salon), "I am a sexual machine now. Raring to go every second of the day. I'm human Viagra. I am Will-agra."

Smith's sexual appetite had not diminished by 2021, when he told GQ that he and an intimacy coach had discussed his desire to have a harem. The "Aladdin" star even shared the names of two famous women whom he would include in it if he were a real-life genie capable of granting his wish: actor Halle Berry and ballerina Misty Copeland. "The idea of traveling with 20 women that I loved and took care of and all of that, it seemed like a really great idea," he said.

Smith has a habit of sharing TMI about his love life. In "Will," he wrote that he once had so much sex that orgasming started to make him vomit, and in his GQ interview, he confirmed longstanding rumors that his marriage to Jada hasn't always been monogamous. "Tons of women would love to have sex with me," he bragged to ABC News in 2001. However, after giving his harem fantasy a little more thought, he came to the conclusion that it would be terrible in reality.

He threw some shade at Slim Shady

When Will Smith bragged about not cursing in his songs in his acceptance speech at the 1999 MTV Video Music Awards, one of the musicians that he beat in the best male video category was Eminem. The prolific profanity user seemingly thought Smith was dissing him, per Rolling Stone, and Eminem later lobbed an expletive at the Fresh Prince in "The Real Slim Shady." In 2000, the Atlanta Constitution asked Smith to address his rival's complaints about his self-censorship. "I'd rather wait five years and let's see who's still here, and then we'll talk about it," Smith said (via The Oklahoman). "I don't have any ill feelings."

Smith stayed true to his word, taking a lyrical shot at Eminem and boasting about the ever-increasing size of his bank account in his 2005 song "Mr. Niceguy." "Dissed by Eminem, but did it bother him? ... Big Will just get another 20 mill' walk right past E," he sings.

Apparently, Smith ensured that his name would one day be spat out by Marshall Mathers' malicious mouth long before the "Lose Yourself" rapper introduced himself to listeners by singing that "God sent me to tick the world off." In an interview with "Montreality," DJ Jazzy Jeff recalled being in a recording studio with Eminem and overhearing Smith telling the up-and-coming artist, "You are either gonna be the biggest flop in hip-hop, or you are gonna be the biggest thing that we have ever seen in hip-hop."

The actor made his oldest son feel 'abandoned'

Will Smith and his son Jaden Smith, whom Will shares with wife Jada Pinkett Smith, clearly developed a close bond from the start; Jaden appeared in his dad's music video for "Just the Two of Us" when he was just a baby and worked on two movies with Will.

But Will confessed that he and his oldest son, Trey Smith, whose mother is Will's ex-wife Sheree Zampino, have had to work harder to build their relationship. "We struggled for years after my divorce from his mother," Will wrote on Instagram in 2018. "He felt betrayed & abandoned." Will updated fans on how he and Trey were doing the following year on his Facebook Watch series, "Bucket List." At the time, Trey was 26. "Really in the last two years has there been enough wisdom and emotional development to be able to lovingly address the issues," Will said. "You cannot get around spending time if you want to build love. It's something I failed at for most of Trey's life, but I'm going to dedicate the rest of my life to making up for it."

The father and son did have some good times when Trey was growing up. On Instagram, Will revealed that they used to film their own "Matrix" spoofs called "The Treytrix" for Trey's birthday even though the movie franchise is a sore spot for Will — he majorly regrets turning down "The Matrix" to star in "Wild Wild West."

Will Smith played a prank on his wife that she didn't find funny

Growing up, Will Smith was concerned about what his grandmother thought of him. In a 2015 appearance on "The Graham Norton Show," Will said he was 12 years old when his granny read some of his earliest, filthiest songs in a book and left him a note that read, "Dear Willard, truly intelligent people do not have to use words like this to express themselves." He stopped using profanity in his songs, but he didn't stop exposing his poor granny to explicit content.

Will appeared on "The Graham Norton Show" again in 2021 and recounted a prank he played on his wife, Jada Pinkett Smith. He put his sinister scheme in motion right before Jada met his granny for the first time. "My grandmother Gigi is all the way down with Jesus. Because she didn't know who Jada was, I put on a movie of hers," Will recalled, per Insider. The movie had a sex scene in it, and Will made sure that his grandmother saw it.

Just like Will, Jada got a dressing down (no pun intended) for engaging in behavior that Will's grandmother didn't approve of. "She looked up and said to Jada, 'When I was growing up people didn't have to take their clothes off to make a movie,'" Will continued. He tried to tell Jada that she would appreciate his hijinks someday, but confessed that she never did look back on the moment and laugh.

Inside Will Smith's ugly feud with a Fresh Prince of Bel-Air co-star

On "The Fresh Prince of Bel-Air," viewers often saw family members putting aside their differences to support one another when they needed it most, but according to actor Janet Hubert, Will Smith made her life so much worse when she was already going through a tough time.

Hubert played Aunt Viv on the sitcom from 1990 until 1993, when she was replaced by Daphne Reid. In 2011, Hubert told TMZ that she believed it was Smith's fault that she ended up losing the role, and her animosity toward him was so strong that she swore she would never participate in a "Fresh Prince" reunion. "I will never do anything with an a**hole like Will Smith," she said. "He is still an egomaniac and has not grown up." She blasted him again in a since-deleted 2016 Facebook post, accusing him of brushing her off when she asked him to help the rest of the cast negotiate better contracts (via CinemaBlend).

Shockingly, Smith and Hubert eventually did make amends during a 2020 HBO reunion special. Per Vanity Fair, Hubert revealed that she was struggling during the time period before she lost her job; she had just given birth and said that her husband was abusive and jobless. Smith apologized for the way he treated Hubert, saying, "I wasn't sensitive, I wasn't perceptive ... I can see where I made the set very difficult for Janet."

The singer got overly aggressive with an NBC executive

It took decades for Janet Hubert to get an apology from Will Smith, but it didn't take long for the actor to realize that he'd screwed up by cursing out one of his bosses. In his book "Will," he recounted how he once decided to make a few of his own modifications to some "Fresh Prince of Bel-Air" scenes that were falling flat. This resulted in Smith getting reprimanded by an unnamed NBC executive.

While Smith described the executive's behavior as condescending and abrasive, he misinterpreted the man's actions. Smith bristled when the exec decided to remain standing for their meeting and got more agitated as the exec walked around the room. Smith reached his breaking point when the exec allegedly said, "You can be gone just as fast as you got here." Smith jumped up, got in his face, and said, "What the f*** you wanna do, bi**h?" He continued shouting at the executive and even ordered him to sit down, and Smith didn't relent when the man told him that he'd just had back surgery.

After he cooled down, executive producer Quincy Jones — the man who possibly saved Smith from financial ruin by pushing him to audition for "Fresh Prince," per "Storytime" – assured him that his outburst was no big deal.

The slap that overshadowed Will Smith's Oscar win

The 2022 Oscars ceremony got flipped, turned upside down when Will Smith decided not to sit right there and listen to Chris Rock make offensive comments about his wife's hair. Every hot take possible was written about the moment Will left his seat, cursed at Rock, and slapped him. And so many celebs had thoughts about it. O.J. Simpson weighed in on Twitter, where he spoke out against Will's violent actions (yes, really). But Will's former "Fresh Prince" nemesis, Janet Hubert, took his side, writing in a since-deleted Instagram post, "Sometimes you have to slap back," per the New York Post.

The drama started when Rock made a joke about Jada Pinkett Smith starring in a "G.I. Jane" sequel, a reference to her buzzed head. Jada rolled her eyes as her husband laughed, but Will's mood suddenly darkened. As noted by ET, Rock's joke likely didn't go over so well with the couple because Jada has alopecia, a condition that causes hair loss. Smith went on to win the best actor Oscar for "King Richard." "I know to do what we do, you got to be able to take abuse," he said in his acceptance speech

The tearful actor didn't apologize to Rock at the time, but he addressed him by name later in an Instagram post. "I was out of line and I was wrong," he wrote. "I am embarrassed and my actions were not indicative of the man I want to be."