John Singleton Told Tupac to Quit Rapping (And 5 More of His Amazing Hollywood Stories)

TheGrill 2017: Academy Award nominee gets candid about Michael Jackson, Spike Lee and “Silence of the Lambs”

Last Updated: October 5, 2017 @ 4:02 PM

Storytelling is John Singleton’s business, but it’s a rare pleasure to hear the groundbreaking director simply tell some stories about his famous friends and collaborators. Like Tupac Shakur and Michael and Janet Jackson.

That’s what was in store for attendees of TheGrill 2017, the annual thought leadership conference thrown by TheWrap that examines strides and challenges in entertainment, media and tech. Singleton sat for a spotlight conversation with TheWrap Executive Editor Tim Molloy, and the “Snowfall” creator got to dishing on his long career.

For starters, he once told the legendary Shakur that he should give up the rap game and pivot to acting.

“I was probably the only person foolish enough to say to him, ‘Why are you rapping?'” said Singleton, who directed Shakur in the 1993 film “Poetic Justice.”

Singleton argued that, at that point in Tupac’s evolution, he was a “better actor than rapper … the crazier his life got, the better he got.”

Tupac’s response to the suggestion? “F— you.”

Read on for five other amazing Singleton anecdotes, starting with …

He Turned Down “The Wire”

Yup, HBO’s seminal cable drama was offered to Singleton and he passed. The director said that, at that time, he thought to himself, “those white people are not going to get it right.”

He confessed to not knowing or trusting David Simon, the police reporter who created the series, or producer Ed Burns. The show looked at the law enforcement, users and sellers in the Baltimore narcotics underbelly.

“I have a sort of prejudice of people not from urban America trying to dramatize it,” Singleton said. He compared urban films to those of Woody Allen, Francis Ford Coppola and Martin Scorsese, saying no one but those auteurs could have possibly made their films. He ultimately decided that “The Wire” got it right.

He also passed on the Michael Chiklis ratings hit “The Shield.” Singleton would get his chance, however, to tackle crime and its deep cultural impact with “Snowfall,” the acclaimed FX drama that mounts a second season next year. It explores the origins of the crack-cocaine boom of the ’80s from a wide range of viewpoints.

He Sold Janet Jackson on a Leading Role That Didn’t Yet Exist

Singleton, a USC Film School alum, recalled “hanging out” on the 1991 set of noted university benefactor Steven Spielberg’s “Hook.”  The pirate ships used in the film were huge practical sets, and many in the industry flocked to visit them.

There, Singleton “ran into” Janet Jackson (and Coppola and George Lucas, for what it’s worth) and on the spot told her:  “I’m doing a movie, I’ve got the script and you’re the star of it.”

Jackson was impressed, gave him her number and said to send the screenplay on over. Except he didn’t have a script at all, and started writing “Poetic Justice” for her right away.

Riding in Cars with Michael Jackson

When Molloy asked Singleton if there was anything Molloy forgot to ask, Singleton noted that the King of Pop hadn’t come up.  He did, after all, helm Jackson’s Egyptian-themed opus “Remember The Time.”

“I think I’m the only person who can say they sat in a car with Michael Jackson and listened to Richard Pryor,” Singleton said.

He also recalled the icon’s childlike wonder, speculating that “he was more obsessed with getting the childhood back he hadn’t had. That was more of an act. When you’re with him, socially, he talked the way a guy from Gary, Indiana would.”

“He used black slang, and he was a really staunch business man,” Singleton added.

Spike Lee Upped His Game 

In the early ’90s, before Singleton would break through with his riveting “Boyz n The Hood,” Spike Lee was considered the only dramatic heavyweight black filmmaker, according to Singleton.

“They needed an alternative to what Spike was doing.” Singleton said of the industry at the time, adding that he’s known Lee since he was in high school.

Singleton got access to a test screening of Lee’s landmark 1989 film “Do The Right Thing,” and said, “I was so intimidated by how good the movie was.”

Right after the screening, “I went to my dorm and started writing ‘Boyz N The Hood’ that day.”

Coolest Day Ever?

One of Singleton’s earliest and most influential mentors was Jonathan Demme, who died in April at age 73. Singleton was invited to a “rough cut” screening of Demme’s masterpiece “The Silence of The Lambs.”

Later that day in L.A., he joined Russell Simmons to meet up with the hip hop group Public Enemy — which consisted of legends like Chuck D and Flavor Flav. There is no other takeaway from this other than it happened in the same 24-hour period, and was probably one of the best days anyone has ever had.

Watch Singleton’s full, uncensored spotlight conversation from TheGrill 2017 below: