[2][5] Levy was convicted of extortion in 1990 on charges from an FBI investigation of alleged infiltration of organized crime into the record business.

It became successful, attracting musicians such as Charlie Parker and Dexter Gordon, and allowed Levy to set up another club, Birdland, in 1949.

[4] At Birdland, Levy was approached by a representative of ASCAP, seeking payment on behalf of songwriters for booking live music.

He then formed a publishing company, Patricia Music (named after his first wife), for which he acquired the rights to songs performed in his clubs.

In 1956, he founded Roulette Records with George Goldner, initially to release rock and roll music but also diversifying into jazz.

[3] In 1967, Levy hired a personal assistant Karin Grasso, the wife of singer-songwriter Richie Grasso (another singer-songwriter signed to Roulette Records) whose work includes "Sweet Cherry Wine", co-written with Tommy James and performed by Tommy James and the Shondells.

[8] Karin assisted in all aspects of Roulette Records, including signing talent and producing music; such as Richie Grasso, Tommy James, Frankie Lymon, and Tito Puente, among many others.

[9] At one point, Morris claimed the rights to the phrase rock and roll itself, which became widely employed after its use by his friend Alan Freed.

After complications due to Spector's erratic behavior, and after attempts at a second agreement failed, Levy used demo recordings by Lennon to produce and release a mail-order album titled Roots.

[11] Beginning in 1984, the FBI targeted Levy in a 3+1⁄2-year investigation into the alleged infiltration of organized crime into the record business.

[14] Earlier that year, near the end of the investigation, Levy sold Roulette Records and his publishing rights (reported variously, for $22–55 million).

[15] Much of the trial evidence came from covertly recorded conversations taken from wiretaps and listening devices planted in the phones and business offices of Levy and Gaetano Vastola.

At his sentencing hearing, his attorneys cited his extensive philanthropic work, while FBI agents testified that Levy had also been a major supplier of heroin for a convicted Philadelphia drug dealer, Roland Bartlett.

"[25] Josh Alan Friedman, the author of a 2008 exposé of the music industry, Tell the Truth Until They Bleed, said that Levy had sent one of his wives to the hospital after beating her in a telephone booth.

According to Fredric Dannen in his book Hit Men, Irving had been stabbed for blocking a prostitute – and wife of an organized crime loan shark – from entering the club.

[45] Levy was played by Paul Mazursky in the 1998 film Why Do Fools Fall in Love, and he was an inspiration for the HBO television series The Sopranos (1999–2007) character Hesh Rabkin[46]—who made a fortune defrauding mostly R&B performers, underpaying royalties, pressing unauthorized records, and who owned lavish New Jersey horse-racing stables.

Levy was also portrayed by David Gianopoulos in the 1999 television film Mr. Rock 'n' Roll: The Alan Freed Story.

Asking to be paid meant intimidation; to survive, those under contract to Roulette needed to find a means of generating income that did not involve the record company, such as personally booked tours.