Hip-Hop in the late 80s was exploding, with Public Enemy urging Black youth to fight the power and N.W.A. screaming "Fuck the police." DJ Jazzy Jeff and the Fresh Prince and Kid 'n Play were keeping things upbeat on the radio and hip-house was moving folks on the dancefloors. But De La Soul was none of the above. 

Regardless of whether you believe "alternative Hip-Hop" is a thing, it's hard to deny De La Soul's 3 Feet High & Rising as a landmark in its development and the first real mainstream success for a quirky, left-field rap act. The Jungle Brothers got there first, but with the radio and chart success of hit single "Me, Myself & I," De La Soul got a broader audience. The album made the trio critical darlings and crossover rap stars. But after two years, 3 Feet High & Rising had become a proverbial albatross around three kids from Amityville's necks. 

By 1991, Pos, Trugoy and Maseo had had enough. De La Soul was fucking tired: tired of being branded "Hip-Hop hippies" by the clueless; tired of being challenged by the streets; and tired of being hamstrung by their groundbreaking debut. For all of the success it'd found and all of the accolades it had been received, 3 Feet High was threatening to pigeonhole De La. With it's Day-Glo cover (something the group themselves hated) and references to "The D.A.I.S.Y. Age" (it stands for "Da Inna Sound, Y'all"), 3 Feet High...saddled De La Soul with an image that they were eager to shuck on their sophomore project. 

They'd already been pushing back against their early image while touring in support of 3 Feet... Producer Prince Paul helmed that project and was hailed for his visionary work with the group, but he was shocked to hear stories of gunplay while De La Soul was out on the road. 

"Random people would come up to me like 'Yo, your boys out on the road - I heard they beat up such-and-such,'" Prince Paul recalled in Mass Appeal's 2016 mini-doc De La Soul Is Not Dead. "I'm like whaaat? Or 'They shot up a car!' I'd hear all these different stories because people knew I worked with them - like 'wow that's crazy.' And I'd ask 'em and they'd be like 'Yeah that's true.'"

“100 percent of the people listening to De La Soul were really attached to the image and not to what we were trying to say," Dave aka Trugoy told Rolling Stone in 1991 just before the release of the group's follow-up to 3 Feet High..., with Pos adding, “We didn’t want to be pinned down to a visual look, and so we thought, ‘This whole daisy thing has to just die.'"

"They were young Black men and they had to deal with all the things that come with being young Black men. They were being marketed in a way that, for them, was emasculating, in a sense. And led them to be stereotyped in a way that would potentially question their "Blackness.'"

The frustration that would forge De La Soul Is Dead permeates throughout the landmark album. Honored with the fabled "Five Mics" from The Source upon its release, the album's subject matter, skits and cover art made it clear that De La Soul was focused on tearing down whatever you thought they were. The end result downplays some of the whimsy of the group's debut, but never completely gives in to the toughness and resentment bubbling just beneath the surface. Prince Paul and the group's chemistry was still strong; albeit with a more defensive slant that some critics found surprising. 

The New York Times posited whether "De La Soul Is Dead Or Just Too Famous?," but the album revealed a group that was still bursting with ideas and their own unique sense of humor. In the album's infamous skits, the group takes on self-consciously hardcore artists, the popularity of watered down hip-house, and their own early image. On the songs themselves, De La addresses everything demo tape-pushing sycophants, to crack addiction to molestation. 

There's an undeniable sunniness to classic tracks like "Keepin' The Faith" and especially the hit single "A Roller Skating Jam Named Saturdays," a song so freewheeling that it feels like it could only come from De La Soul. The album's conceit is that De La Soul is wack and thus, "dead," a phrase uttered in a recurring skit by a school bully (played by Mr. Lawnge of Black Sheep) as he torments some kids for owning a De La tape. 

“It’s not the same feeling as 3 Feet..., where as soon as you put the needle on the record, you jumped to it," Dave said in that Rolling Stone interview.

"But I think people will have faith in us and say, ‘Let’s listen to it for a little while, let’s see what’s really happening.” 

Prince Paul's production ear feels more assured throughout ...Dead, even though the commercial reception to the album (it wasn't the runaway hit that 3 Feet High... had been) frustrated Paul so much that he retreated into a passion project called Gravediggaz that would all but invent horrorcore. 

“We wanted to show the one side that, yo, it ain’t gotta be a rough beat all the time," Maseo said in 1991. "And let the other side know there is a rough side.”

The smashed flower pot of daisies on the cover has always made it clear: De La Soul isn't trying to stay where you've planted us. Their sophomore album was them committing a mock execution on their own image and also on the way they felt they'd been handled by their label, Tommy Boy. That bold act helped free them creatively, and it set the stage for the remainder of their decades-long career. 

"With the success of 3 Feet High And Rising, we were worked a lot,” Maseo recalls of their management duo – Def Jam founder Russell Simmons and Lyor Cohen, who is now YouTube’s global head of music. “There wasn’t really room to go back into the studio and make more music. And what was going on with D.A.I.S.Y. Age, what we’d intended to be a movement felt more like a trend, a misinterpreted trend. Trends come and go – we wanted to kill that trend before it killed us.”