The late 1980s/early 1990s are an interesting time in popular culture, particularly in movies. After the monster successes of generation-defining franchises like Star Wars and Indiana Jones, the blockbuster approach was running rampant in Hollywood; but the mainstream movie industry hadn't yet gotten fully corporatized and homogenous. There were still some studios willing to take a chance on making very expensive, very odd movies. Oddball Tim Burton movies like Beetlejuice and Edward Scissorhands were major successes; but they weren't the only big, strange films getting made. And there wasn't a bigger, stranger movie than 1991s bizarro comedy Nothing But Trouble.

Developed as a horror-comedy by Dan and Peter Aykroyd, the story was inspired by an incident where Peter was pulled over in upstate New York and had to go before a justice-of-the-peace in a podunk town. Around that episode, the Aykroyd brothers crafted one strange movie. ...Trouble is the story of a snooty Manhattan publisher (Chevy Chase) and a lawyer (Demi Moore) that he's got his eye on; who get ticketed for speeding while driving through Valkenvania, New York, with a fashionable Brazilian brother and sister (Bertila Damas and the late Taylor Negron.) The Valkenvania courthouse they're taken to is a cross between an Eastern European stronghold and something out of The Texas Chainsaw Massacre; and things only get weirder, as Dan Aykroyd does double duty as grotesquely ancient Judge Alvin Valkenheiser and one of two giant, greasy mutant babies, (named Bobo and Lil Debbull) and the legendary John Candy also plays two characters: as the judge's police officer son Dennis, and near-mute daughter, Eldona—who, incidentally, Chase is forced to marry.

In the middle of all of that strangeness—once again, there is a pair of giant, greasy, diaper-wearing mutant babies in this movie—Digital Underground shows up. In the context of the movie, Shock G. and Co. are a group of musicians who, like our main stars, get pulled over in Valkenvania and find themselves going before Judge Valkenheiser. Unlike our protagonists, however, they can use their musical gifts to jam their way out of a jam.

Of course, in actuality, Digital Underground was enjoying tremendous success on the heels of their 1990 debut album Sex Packets, and their monster hit single, "The Humpty Dance." Aykroyd always had a fondness for including Black music in his films: The Blues Brothers is essentially an homage to 60s soul music; rock & roll legend Bo Diddley memorably cameoed as a pawnbroker in Trading Places; the Ghostbusters theme was written and sung by R&B/jazz star Ray Parker, Jr.; and it's sequel prominently featured a soundtrack stocked with Hip-Hop and R&B acts like Run-D.M.C., New Edition and, perhaps most notably, Bobby Brown. During an appearance on The Arsenio Hall Show to promote the movie, the former Saturday Night Live star shared his enthusiasm for D.U.'s appearance in the film.

“Digital Underground joined us, we commissioned a song with them,” Aykroyd explained. “I wrote a scene in the movie where this 106-year-old justice of the peace that I play in the film runs across these musicians, they come into his compound…So, I wanted a talented group to commission and write a song for the film.”

The song Digital Underground delivered, "Same Song," would become the most memorable scene in the movie and a hit single for the group. Shock G's loosely funky production and laid-back flow sits centerstage, as his alter ego Humpty Hump makes an appearance, alongside Money B and a young rapper who was new to the group. Tupac Shakur had joined Digital Underground just as they were about to head out on tour in support of Sex Packets, and he and Shock bonded immediately. Now, 2Pac was getting his first chance to shine on a D.U. song, and his verse announced the up-and-coming emcee in star-making fashion.

“Dan Aykroyd, he always has musicians in his movies," the D.U. frontman explained. "So Dan pops up at one of our shows. This is mid-summer and ‘Humpty Dance’ came out. We’re, like, hot as fuck right now…And the person to my left said ‘You want to spark a doobie?’ And I look over and the first thing I see is the little white twisted-up old-school blunt, used to be a ‘doobie,’ they called it. I looked further to my left and see the face holding it, and it was fucking Dan Aykroyd! He passed me the weed, I hit it and passed me it back. We passed it around the room. And that’s when they said, ‘We got this movie thing.’ Are you kidding me? Anything you want to do. I’m such a huge fan.”

2Pac was becoming a bigger part of D.U.'s plan; as Shock looked to expand the group into offshoots that included the duo Raw Fusion and Pac's solo career. They would start work on 2Pacalypse..., but the young rapper, who'd moved to the Bay Area from Baltimore as a teen, was impatient.

"Outside of working with him, I didn’t see him much," Shock G said in 2017 of his initial time with Pac. "I saw him every time I was in the studio with him – and even then didn’t see him much. Cause he would just pace, and he’d come back in the room. 'Is the beat ready yet? Goddamn.' Restless. He’d go outside and smoke. Go across town or something. He’d come back. 'Yo, can I rhyme? Can I rhyme?'”

As the group was putting the finishing touches on This Is An EP! Release (a stopgap Extended Play to whet fans' collective appetites after the success of Sex Packets), "Same Song" became a perfect opportunity to showcase Pac.

"Unlike most artists who want to sit there as we figured out where the string line is going, he didn’t sit for each listen," Shock shared. "He would come back out of the booth and listen one time down. Once we started selecting reverbs and levels and all that, he would get bored and just tap me on the shoulder and say, 'Alright, make that shit dope.'"

Nothing But Trouble famously bombed at the box office and with critics. The movie was gasoline on the house fire that was Chase's movie career at that moment; a major failure in what was turning into a series of failures for Hollywood's onetime king of comedy. It was a significant stain on Aykroyd's resume, as well; he wouldn't have the kind of creative clout in the 1990s that he'd enjoyed in the 1980s, which had yielded beloved films like Blues Brothers and Ghostbusters. Aykroyd's flirtations with Hip-Hop didn't end at "Same Song" (he also appears in the madcap video alongside Digital Underground and Eazy-E and Dr. Dre of N.W.A., who also cameo); he would feature Erykah Badu in the ill-fated Blues Brothers 2000 and did drops for DJ Whoo Kid's G-Unit mixtapes in the early 2000s.

The movie may have almost killed its star's careers (Moore largely emerged unscathed, and after smashes like A Few Good Men and Indecent Proposal in 1992 and 1993, respectively, she went on to become one of the biggest box office stars of the 1990s), but the success of the single was a win for D.U. and 2Pac. "Same Song" was part of a creative peak for Digital Underground and it launched 2Pac into orbit. A year later, he would release his solo debut 2Pacalypse Now and kickstart a legendary career as both rapper and actor.