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Jim Belushi and Tupac nearly collaborated on a cover of Frank Sinatra's 'Fly Me to the Moon'

·5 min read

When Tupac Shakur arrived late to a rehearsal for the film Gang Related in 1996, his costar Jim Belushi called him out. Although the pair's relationship got off to a rocky start, they went on to form a bond that nearly resulted in the unthinkable: a musical collaboration.

"As prolific as he was as a musician, Tupac had never really heard Frank Sinatra," Belushi tells EW exclusively. "So I brought my The Golden Years CD [to set] and we listened to it in the trailer. When we hit 'Fly Me to the Moon,' I said to him, 'Come on, man, let's write a song. We can do "Fly Me to the Moon" with you rappin', a blend with an old ballad and your style of rap.' We worked on it between scenes."

Belushi wasn't new to the rap game when he and Shakur starred in the Jim Kouf-directed project. Here, the actor-turned-cannabis farmer (the career move was not inspired by Shakur) reveals how a trip to the movies changed his life and inspired the popular Rappin' Jimmy B sketches on Saturday Night Live.

Jim Belushi and Tupac Shakur in 'Gang Related'

ENTERTAINMENT WEEKLY: Your recent tweet about sharing a sunrise with Tupac shocked fans who didn't know you had worked together. What can you share about that moment?

JIM BELUSHI: We were shooting all night on Gang Related and wrapped as the sun was rising. We were sitting there smoking a cigar, and I just loved what he said. It made me laugh.

He looked over at you and said, "I'm a thug. I prefer the sunrise." What had you guys been discussing at that moment?

During that sunrise, we were having a talk. When he said that, it was a non sequitur. We weren't talking at that moment, just watching. Then he popped out with that.

What was the talk about?

As prolific as he was as a musician, he had never really heard Frank Sinatra. So I brought him my The Golden Years CD and we listened to it in the trailer. When we hit "Fly Me to the Moon," I said to him, "Come on, man, let's write a song." We can do 'Fly Me to the Moon' with you rappin,' a blend with an old ballad and your style of rap."

He was so impressed by Sinatra. We worked on it in between scenes, and we were talking about it during that sunrise. But he later said, "I can't do it." And I was like, "What do you mean you can't do it?" He said, "It's too melodically beautiful to interrupt. There's just no way. It's too perfect of a song to mess with." My response to him was, "Well, now you get Frank, don'tcha?" We didn't get far into this project, but we toyed with the idea of collaborating. We entertained each other on the set.

What could've been! Were you a fan of rap music before you met him?

I was a fan of Grandmaster Flash, way back when I was on Saturday Night Live. I actually did the first rap parody called Rappin' Jimmy B (below) and then the White Guys Rap. I remember watching this movie called Wild Style in Times Square, this movie about graffiti that had break dancing and house music. I couldn't think about what to write for Saturday Night Live in like '83, '84. So my buddy Chris Barnes and I went to see this movie, and we walked out of there, and we were rapping! We were freestyling down the street. That's how we came up with Rappin' Jimmy B. I remember I hired this 16-year-old kid from the Bronx and he showed me how to break-dance. I did the spins and the jumps. I can still do them.

Did you ever freestyle for Tupac?

I busted his chops all the time. I told him that I'd been rapping since he was coloring with crayons in grade school. I did my whole white-guy rap for him and he laughed so hard. What I loved about him is that he was a poet, he was a writer. He wrote about the culture and very personal things: women, his mother, the community, and the struggle. I was already a fan of his music before we worked together. At the time, there were a lot of rappers singing about being an MC. It was a lot of "me, me, me." But Tupac was all about the world around him, and it was beautiful and moving.

He was such a great lyricist. One of my favorite songs he did is "Wonder Why They Call You Bitch." That one breaks my heart every time I hear it. I also love "Dear Mama" and "Shorty Wanna Be a Thug." [Belushi starts singing the song.] I love "Shorty Wanna Be a Thug."

How long after the film wrapped did Tupac die?

He died 10 days after we finished shooting. I was in Australia at the time, where I was shooting some commercials. Oh my God, it was so heartbreaking.

He died so young, and with so much potential.

Yeah, I feel that way about my brother [John Belushi] too.

And Tupac wasn't the only rapper on set. Kool Moe Dee also worked on Gang Related, right?

Yeah, we only had him there one day, but he was super cool.

That's a rap trio that could've been.

Yeah! [Laughs] We should've had a rap party together. We had a lot of fun teasing each other.

This interview has been edited and condensed for length and clarity.

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