Redman’s album, Dare Iz a Darkside, turned 20 years old this weekend (11/22). True to its name, Red’s sophomore album was an exploration through a deep, dark funk sonically. The album, produced primarily by Reggie Noble himself with some help from Erick Sermon and Rockwilder, drew heavily on Red’s love of the raw and guttural sounds of the P-Funk. He makes his intentions clear on opening song “Dr. Trevis” where he says: “I want you to concentrate very hard on how you will do the second album. I want you to take the funk where it has never gone. I want you to take this LP to where no other mother-LP has risen.” The album also found Red in a dark place, visually. The cover, an ode to Funkadelic’s Maggot Brain, showed him neck deep in dirt as if trying to ascend from being buried alive.

After a star-making guest verse on EPMD’s “Headbanger” and his gold-certified debut Whut? Thee Album, there was incredible anticipation for Redman’s second LP. The Newark, New Jersey MC had already established himself as one of Hip-Hop’s best and brightest, even in an era that included artists like The Notorious B.I.G., Nas, Wu-Tang Clan, OutKast, Mobb Deep, Snoop Dogg and countless others.

Like its predecessor, Dare Iz a Darkside also sold north of 500,000 copies, but it was an artistic departure from the primarily lighthearted first album. Lyrically, Dare Iz a Darkside was one of Redman’s most inscrutable with free flow songs like “Journey Throo Da Darkside” and “Wuditlooklike.” In the midst of the dense “Cosmic Slop,” the album also yielded one of Redman’s most enduring hits to date, The Mary Jane Girls-driven “Can’t Wait.”

While Dare Iz a Darkside remains a fan favorite, Redman is more ambivalent about the LP and that era generally. When speaking to HipHopDX about the project in 2010, Red said: “I was doing a lot of drugs on Dare Iz A Darkside. I have chicks that come up to me and say, ‘Yo, Dare Iz A Darkside is my favorite fuckin’ album, ever.’ I swear, I have not played Dare Iz A Darkside damn near since I did it. Seriously! I was so lost, I was so fucked up during that album.”

Twenty years later, symbolically to the album cover, Redman has ascended from the darkness of Dare Iz a Darkside. What remains is one of Hip-Hop’s most enduring and endearing MCs and one of its most daring albums.

Related: Redman Shows How He Rocks on a Doug E. Fresh and Slick Rick Classic (Audio)