Paul was interested in music from a young age and started collecting vinyl when he was five. According to his late mother, he was mature for his age and tended to hang out with older friends.
When he was in fifth grade he started DJing, using a makeshift setup of one Lafayette turntable hooked up to another turntable set and using the balance knob as a fader. In 1981, at age 14, Paul performed a DJ set at The Ace Center Amityville that helped him gain recognition. He did a routine with Trouble Funk’s “Pump Me Up” which he later described as his “claim to fame.” After The Ace Center performance Paul started doing parties and tapes with Biz Markie while he was in 8th grade. At the same time, Paul’s middle school music teacher was Everett Collins, a drummer for The Isley Brothers. Collins later introduced Paul to De La Soul member Maseo.
He began performing with groups during his teenage years, first joining a group called Soul Brothers with his longtime friend Don Newkirk, who would later re-join Paul as an official member of Brookzill!Paul was one of the original members of Stetsasonic. He joined the group in 1984 after impressing Daddy-O with his routine in the “Brevoit Day Celebration” DJ battle in Brooklyn. Daddy-O was struck by Paul’s energy, saying that he performed his routine with Liquid Liquid’s song “Cavern”, “like he was mad at the turntables.” Paul credits Grandmaster Flash’s song “Flash To The Beat” as the reason he purchased his drum machine.
Prince Paul produced “The Gas Face” and “Brooklyn-Queens” on 3rd Bass‘ 1989 debut The Cactus Album. The original version of “The Gas Face” was recorded on 4-track cassette tape and started out as mistake. Paul wanted to change the beat after he realized the pattern wasn’t what he wanted but MC Search and Pete Nice convinced him to keep it. The song was recorded on the 4th of July.
He also worked on De La Soul‘s first three albums, 3 Feet High and Rising (1989), De La Soul is Dead (1991), and Buhloone Mindstate (1993). De La Soul is Dead received a five mic album review from The Source (magazine). According to Paul, 3 Feet High and Rising (1989) had a budget of about $20,000 dollars and took a month and a half to make. In Brian Coleman’s book Check the Technique (2007) Paul reflected on his work with De La Soul by saying, “If there was ever a sign of the existence of God, De La Soul would be that proof to me. I’ve never had such a perfect fit in any other production situation.”
In 1992 Paul produced the songs “Drug Dealer”, “Sex and Violence”, and “How Not To Get Jerked” for Boogie Down Productions’ Sex and Violence album. Paul later expressed frustration over the experience of working on that album because the group released the album before he had a chance to finalize and polish his songs. KRS-One later apologized to Paul.
In 1993 Paul co-produced De La Soul’s Buhloone Mindstate. Successful comedian Chris Rock, who would later work with Chris Rock on several of his albums, listed the album as #10 on his “Top 25 Albums” list. He credited album as helping to shape him as a comedian.
Along with Frukwan of Stetsasonic, Too Poetic of Brothers Grimm, and The RZA of Wu-Tang Clan, Prince Paul formed the group Gravediggaz. They recorded a demo together in 1991 and released their first album Niggamortis/6 Feet Deep in 1994 on Gee Street records. Before signing a deal with Gee Street, Eazy-E wanted to release the album on Ruthless Records. Paul flew to Los Angeles to have a meeting with Eazy-E and Jerry Heller but felt the contract offered to him was one of the worst he had seen in his career and declined. After the group signed to Gee Street, Paul estimated that it took them about six months to complete the album.
In 1995, Prince Paul co-produced guitarist Vernon Reid‘s solo debut with Teo Macero. He also produced an the Horror City album with Amityville rapper Superstar. After recording the demo, Paul unsuccessfully shopped it around to multiple labels. Paul used some of the same instrumentals on A Prince Among Thieves and had some of the same people rap on the album, but later said he preferred the Horror City originals. In 2010, after holding on the demo for 15 years, Paul decided to offer it as a free download online.
In 1996, he appeared on the Red Hot Organization‘s compilation CD, America is Dying Slowly, alongside Wu-Tang Clan, Coolio, and Fat Joe. The CD, meant to raise awareness of the AIDS epidemic among African American men, was called a masterpiece by The Source magazine.
In 1996, during the early recording sessions for Stakes Is High, De La Soul and Prince Paul decided to part ways. Although Paul was not involved in the making of the album, he has praised it in several interviews, once saying, “I was going through a serious transition period in my life when that album dropped. I was trying to figure out the next thing I was going to do; I was going through a custody case for my son, and I was running out of money. There were a lot of things going on at the time and in a sense, that album pulled me through everything.”
After this he released two solo albums: Psychoanalysis: What is It? and A Prince Among Thieves, featuring Big Daddy Kane, Xzibit, Kool Keith, and Everlast. When Paul was recording Psychoanalysis he thought his career was over and had a hard time finding people who wanted to be involved with the project. Many of the vocals were provided by friends of his from outside the music industry. Years later he recalled thinking, “Some people might get butt-hurt about it, but so what? It’s probably the last record I’ll make anyway,” during the recording of “Beautiful Night (Manic Psychopath)”. The song is very dark and deals with date rape, racism, and violence.
According to Paul, he originally proposed the idea for A Prince Among Thieves to Russell Simmons in the early 90s but Simmons wasn’t interested. While describing his goals for the album in an interview he said, “I wanted to make a movie on wax. I wanted to make an adults’ kid album.” To prepare for the album he watched many B movies and tried to use scenes from various films as inspiration. In addition to the extensive list of rappers on the album, Paul reached out to Vanilla Ice to perform on “Handle Your Time with Sadat X and Xzibit. He also reached out to The Notorious B.I.G. about playing a role on the album and was supposed to meet up with him the night he was murdered.
Prince Paul formed Handsome Boy Modeling School with Dan the Automator and their album So… How’s Your Girl? featured Sean Lennon, Del tha Funkee Homosapien, Alec Empire, and Don Novello. He was also paired up with Deltron 3030 on their self-titled album for the song The Fantabulous Rap Extravaganza. In 2000, Prince Paul produced MC Paul Barman‘s début EP It’s Very Stimulating, followed by another Handsome Boy Modeling School album, White People, with guests including the RZA, Linkin Park, Tim Meadows, and John Oates.
Prince Paul’s 2003 album Politics of the Business again featured many guests such as Chuck D, Ice-T, the Beatnuts, and Wordsworth. The latter also collaborated on a track Paul composed for the SpongeBob SquarePants Movie soundtrack.
In 2005 Paul won a Grammy award for his work on Chris Rock’s Never Scared album, the first of his career.
His most recent release is the album Itstrumental. It encompasses a range of genres, relying heavily on past samples, especially from A Prince Among Thieves, and combining them with lighthearted skits about his depression. He also produced the album The Art of Picking Up Women by the Dix, which combines some of hip-hop’s misogyny and boasting with 1960s-style R&B.
Paul was the host of XM radio’s “The Ill Out Show”, until the station was dropped following its merger with Sirius. The show presented news, classic songs, and interviews with various hip-hop artists.
One of Prince Paul’s more recent projects is Baby Elephant, a collaboration with Parliament and Talking Heads keyboardist Bernie Worrell, and longtime Paul associate Don Newkirk. An album Turn My Teeth Up!, released in September 2007, features George Clinton, Shock G, Yellowman, Reggie Watts, Nona Hendryx, David Byrne, and Gabby La La.
In 2008–2009, Paul collaborated with Oakland rap group Souls of Mischief on the group’s album Montezuma’s Revenge (2009). The idea for the album came about during a Handsome Boy Modeling School tour when Paul told Souls of Mischief member Opio, “Tell the guys that I want to produce the next album.” The album was recorded in a rented house and many of the beats were made with vintage equipment, including a Emu SP-12, Ensoniq ASR-10, Akai MPC-60 and an Akai MPC-2000. Paul stated in an interview that his two favorite songs from the album are “Proper Aim” and “Morgan Freeman Skit”.
In 2012, Paul spoke openly in an interview about the possibility of doing another De La Soul album after Maseo had made some public comments about a reunion. In the interview, Paul states that he asked the members of De La Soul to work on a new album on and off since 1999. Though he wanted to do a reunion at one time, it seemed in the interview he had moved past the idea, partially because of the far more restrictive sampling laws that exist today. He said, “It’s nice to think about it, but I kind of like where we left it. There would be so many expectations. For me to do another De La record, I don’t think I could really live up to it. Especially in a day and age where I can’t openly sample like that.”
Paul later released Throwback to the Future with his Brazilian hip hop fusion group BROOKZILL! in 2016. In 2017 Prince Paul helped score the Gimlet Media podcast Mogul about hip-hop scene-maker Chris Lighty.