Licensed To Ill, their 1986 debut album, had made the trio of Mike D, Ad Rock and MCA the unlikeliest of rap superstars. But as that album barreled it's way to diamond-selling success (en route to becoming the best-selling rap album of the 1980s), the Beasties found themselves trapped in their cartoonishly frat boy-friendly images. And they were also trapped in an increasingly-tenuous situation with their record label, Def Jam Recordings.

The blockbuster returns from Licensed To Ill hadn't led to critics and detractors taking the Beastie Boys seriously. Quite the contrary: the trio was regularly dismissed as an obnoxious novelty act, coasting on the talents of Def Jam superproducer Rick Rubin. And after the notorious Licensed To Ill Tour, their goofball, party animal image was cemented. And it was encouraged by Def Jam.

“Seemed funny at the time," Ad Rock would recall in the group's 2018 memoir, Beastie Boys Book. "[But] you gotta really think before you say or do some dumb shit. Think about the people you care about most. Will they be embarrassed for you, and of you? Yes . . . And you’ll end up paying thirty years’ worth of storage locker fees in New Jersey for a 5-foot-by-5-foot dick in a box.”

The group was getting tired of spraying beer in their faces onstage. And Def Jam was demanding a second album. The frustrations were beginning to come to a head. "Yeah, man, it wasn't about having to do a job and having to play live," Mike D explained to The Guardian in 1989. "But after a while [labelhead] Russell [Simmons] would be sticking beer in our hands and saying 'Go … this is what you get paid to do.'"

"That's bullshit," Adam "MCA" Yauch interjected. "Russell never put shit in my hands."

"No, I remember it," Ad Rock countered. "You guys were there and we got into a big argument. He said: 'You didn't drink beer last night. At least go out there and tap a beer, catch a beer.'"

"We were like: 'Fuck you, Russell, that's not what we're about.'" Mike shared. "In England, we were depicted as larger-than-life villains, and by the time we got to Liverpool, those people weren't there to see the music. They were there because of what they'd heard about it and they were psyched to fuck shit up on a Saturday night, and the people we were working with could've steered us away from that but they didn't and only now can we look back and see that certain things had led us to that point. But you can't control it … life is way stranger than fiction."

They group splintered somewhat as Ad Rock ventured to Los Angeles to dabble in acting. MCA would soon also make his way to the Golden State, and by the time Mike D joined his bandmates in L.A., the seeds were sown for shift. The Beasties would land on Capitol Records, with a new focus, and a desire to try new things. Ad Rock had heard a mixtape by a production duo who called themselves the Dust Brothers; Mike Simpson and Matt Dike, and was eager to work with the pair.

"Yauch and Mike Simpson went to school together in New York years ago, but we didn't even know he was in the Dust Brothers," Mike D told The Guardian back in 1989. "We met Matt Dike way back at Power Tools … "

"When we met him, Matt was dressed in a fucking witch's costume … it was a week before Halloween and my man just busted out with full witch gear – the hair and the pointed hat and a short black dress," added MCA.

Lead single "Hey Ladies" was the perfect appetizer for what the Beasties and Dust Brothers were cooking up. With a random-but-inspired lift of a cowbell from Jeanette “Lady” Day’s "Come Let Me Love You," the Beasties stretch and parody their own quasi-macho images while delivering a music video that effectively establishes the winking oddness of where they were going aesthetically. The second project from the Beastie Boys would eschew the over-the-top antics of Licensed To Ill for something much more idiosyncratic and offbeat; the in-jokes were more obscure, references more unapologetically quirky. And armed with the Dust Brothers sonic arsenal, the sampling would be a stylistic free-for-all, guided by the Boys' stream-of-consciousness approach to creativity.

"Hey Ladies" would be the closest Paul's Boutique would come to a hit. The single peaked at only #36 on theBillboard Hot 100, but was notable as the first single to chart in the top 20 of both the Hot Rap Singles and Modern Rock Tracks. It remains one of the band's grooviest singles, and a testament to the creativity of the Dust Brothers.

The Dust Brothers had a treasure trove of beats that they'd been sitting on; showcasing a gift for collage-style sampling that echoed what would be heard on Public Enemy's 1988 masterpiece It Takes A Nation Of Millions To Hold Us Back and De La Soul's 3 Feet High & Rising a year later. But Dike and Simpson had their own spin, and when married to the Boys' personas and own need to shuck their previous image, it made for a bold new direction for the Beasties. Album tracks like "Egg Man" and "Sound Of Science" were bursting with an unbridled creativity. The album's other's single, "Shake Your Rump," boasted snippets from disparate sources like “Funky Snakefoot” by Alphonse Mouzon to “Jazzy Sensation” by Afrika Bambaataa and The Jazzy 5 and “Get Off” by Foxy.

"They had a bunch of music together, before we arrived to work with them," Yauch explained years later. "As a result, a lot of the tracks on Paul’s Boutique come from songs they’d planned to release to clubs as instrumentals— ‘Shake Your Rump’, for example. They’d put together some beats, basslines and guitar lines, all these loops together, and they were quite surprised when we said we wanted to rhyme on it, because they thought it was too dense. They offered to strip it down to just beats, but we wanted all of that stuff on there. I think half of the tracks were written when we got there, and the other half we wrote together.”

“Egg Man” flips the iconic bassline from Curtis Mayfield’s “Superfly” alongside the theme from Jaws; and album standout “High Plains Drifter,” melds “Those Shoes“ by the Eagles, “Your Mama Don’t Dance“ by Loggins and Messina, and “Put Your Love (In My Tender Care)” by The Fatback Band. "Looking Down A Barrel Of A Gun" boasts Mountain’s “Mississippi Queen” as a kickoff. The album closer is the epic "B-Boy Bouillaisse," a heady mix of song snippets built around a little bit of everything; the Isley Brothers, the Beatles, boom bap, Keith Tex and so much in-between.

“'B-Boy Bouillabaisse' needed to be on the record," Mike D said in 2019. "It’s so unique. We went for it. We had this ambition, and we made it happen. We loved short songs at the time—some of our favorite Ramones songs are two minutes, and some of our favorite hardcore songs are a minute and a half."

When it was released in the summer of 1989, Paul's Boutique was a massive flop for Capitol and the Beastie Boys. The Hip-Hop landscape had changed significantly since Licensed To Ill in 1986, and "Hey Ladies" was such an oddball lead single that audiences didn't really know what to make of the Beasties 2.0. Def Jam had quickly moved on to Long Island trio 3rd Bass, and the Beasties suddenly looked like yesterday's white rap group.

“We put every idea that he had into that record, every sample, everything that we thought was funny to each other,” Mike D told a Tonight Show panel in 2020. “It’s like that thing where you work really hard on a record and you think it’s dope…and we put it out and it’s crickets.”

At the time, the Beasties were overshadowed by virtually everything else happening in rap circa 1989: acts like Public Enemy, EPMD and De La Soul. Decades later, Paul's Boutique is hailed as a masterpiece; a stellar example of a group forcing itself out of the box it had once gladly locked itself into. And it sets the stage for the Beasties' eclectic 1990s comeback, where they forged a legacy as alt-rap godfathers, while also carving a niche for genre-bending contemporaries like Beck and Lucious Jackson. It all started with ...Boutique.

"We were so excited working on Paul’s Boutique," Mike D told INTERVIEW Magazine in 2019. "And we had this expectation because we’d had a hit record before it. So we thought, 'Of course it’s going to connect with people because that’s what happened with our last one.” And then it came out and absolutely did not. Looking back at it now, it makes a lot of sense to us why it didn’t, because even though we were super into it and eventually other people were into it too, it’s nothing like Licensed to Ill..."