Willard Carroll Smith II, better known as Will Smith, or his stage name The Fresh Prince, has been in the entertainment field for 35 years. As of 2022, his films have grossed over $9.3 billion globally, making him one of Hollywood’s richest stars. Smith started out as the MC of the hip-hop duo DJ Jazzy Jeff & the Fresh Prince, with his childhood friend Jeffrey “DJ Jazzy Jeff” Townes as turntablist and producer.

The duo’s first album, , was first released in 1986. The group received their first Grammy Award for Best Rap Performance in 1989 for “Parents Just Don’t Understand” (1988). But though their most successful single was “Summertime” (1991), which earned the pair their second Grammy.

With success, Smith spent money more freely and around 1988 and 1989 he underpaid his income taxes. The Internal Revenue Service eventually assessed a $2.8 million tax debt against him. Many of his possessions were taken to pay off his debt. Smith admitted that he had to borrow $10,000 from a drug dealer when he became broke.

Smith was struggling financially in 1990 when the NBC television network signed him to a contract and built a sitcom around him. He starred as a fictionalized version of himself on the NBC sitcom  (1990–1996). The show was successful and began his acting career.

Smith set for himself the goal of becoming “the biggest movie star in the world.” But his stratospheric rise to Hollywood stardom almost did not happen had it not been for an encouraging girlfriend.

Will Smith Was Arrested In 1989 For An Alleged Assault

A year before signing onto , Smith was arrested over an alleged assault that took place in Philadelphia. Smith, who was 20 at the time, was involved in an argument that resulted in the man almost losing sight in one eye. The charges against the 54-year-old actor included aggravated assault, criminal conspiracy, simple assault and recklessly endangering another person.

Smith allegedly asked his bodyguard, Charles Alston, to attack record promoter William Hendricks, who needed six stitches after he fractured his left eye orbit during the attack. “Will had to spend a night in the cell at the West Philadelphia police station with other inmates waking him up all night long and asking for his autograph. It was the worst night of his life. He wants to forget it ever happened,” reports. The charges were later dismissed.

“Before I was in trouble with Uncle Phil, I was in trouble with Uncle Sam,” Smith joked in a “STORYTIME” video on his official YouTube channel. Smith admitted to a frivolous lifestyle at the height of his success as a rapper. He was buying motorcycles and cars and, most importantly, not paying his taxes. His career as a rapper was suddenly in decline, and he was left broke and at the mercy of the IRS.

His girlfriend at the time convinced him to make an appearance on “The Arsenio Hall Show.” There he met record executive and talent manager, Benny Medina, the man who “Fresh Prince” was based on. Smith was invited to meet legendary music producer Quincy Jones who handed Smith a screenplay. He asked him to audition for the lead role of on the spot. The rapper asked for a few weeks to prepare for the role to which Jones replied, “you could take 10 minutes right now, and you could change your life forever.”

Needless to say, Smith won the role and the rest is history. “The moral of the story is always say yes. And I guess, listen to your girlfriend,” Smith told his almost 10 million YouTube followers.

Will Smith Calls His Acting In The First Few Episodes Of ‘Fresh Prince’ ‘Terrible’

Will Smith had no acting experience before he took on the role on the  When talking toabout his early performances he said, “It’s terrible, and I can’t bear to watch it.”

According to  Smith learned not just his lines but the whole script. In the earlier episodes, you can actually see him miming his co-stars lines! “It was my very first role, and I was very, very focused on being successful, so I learned the whole script and everyone else’s lines.”