Levy grouped Gee, Rama and Tico into Roulette Records. Some years later, Levy also bought Gone Records and End Records from Goldner. In 1958, Roost Records was purchased. In 1971, Roulette took over the catalog of Jubilee Records.

History
During the late 1950s, Roulette scored hits by Buddy Knox, Jimmy Bowen, The Playmates, Jimmie Rodgers, Ronnie Hawkins as well as albums by Pearl Bailey, Dinah Washington and Count Basie.

During the early 1960s, Roulette issued a number of hits connected to the twist dance craze, most notably by releasing "Peppermint Twist" by Joey Dee and the Starliters. They also released a rare album of "Twist songs" by Bill Haley & His Comets, Twistin' Knights at the Roundtable. Other major 1960s hits for the label include "Two Faces Have I" by Lou Christie, "Mony Mony", "Hanky Panky", "I Think We're Alone Now" and "Crimson and Clover" by Tommy James and the Shondells, among others. It was also on the Roulette label that, in 1964, Stephen Stills and Richie Furay first recorded together while in the nine-member A Go Go Singers, house band for the Cafe A Go Go in New York. And a group of United States Marines called The Essex recorded the hit "Easier Said Than Done" while based at Camp LeJeune in the 1960s.

According to Tommy James of Tommy James and the Shondells, during his time at the label, Roulette was a front business for the Genovese crime family. James estimates that the label kept $30 million to $40 million of the group's royalties, but afforded it total artistic freedom whereas another label would have tampered with its formula and might have dropped the group early on.

In April 1965, the British music magazine, NME reported that Roulette had agreed to offer a sponsored show to the UK's pirate radio station, Radio Caroline. The hour-long show, recorded in the U.S. by DJ Jack Spector was to be broadcast five evenings a week. The contract covered a two-year period and was worth over £10,000 to the station.

Throughout the 1960s and 1970s, Roulette was one of the major distributors, handling records for many major firms.

Levy was the key financial backer for the rap music label Sugar Hill Records which was founded in 1974 by husband and wife Joe and Sylvia Robinson. Sugar Hill released the first Top 40 rap single, "Rapper's Delight," in 1979. In the early 1980s, the Robinson's bought Levy out.

In 1981, Henry Stone turned to Levy to help salvage the demise of TK Records, so they set up Sunnyview Records under the Roulette umbrella. In 1986, Levy was exposed and convicted for extorting money from an FBI informant, John LaMonte. Levy was tried and convicted on charges of extortion but died in Ghent, New York before serving any time in prison. In 1989, Roulette Records was sold to a consortium of EMI and Rhino Records, which later were acquired by The WEA Group (Warner/Elektra/Atlantic). Warner Music Group now has the rights to the Roulette pop/R&B catalogue in North America, while EMI has the rights in the rest of the world. EMI has the global rights to the jazz catalogue and the "Roulette" name.

Following the acquisition Rhino and EMI began issuing large royalty checks to former Roulette artists. Tommy James recalled that his checks were in amounts in six or seven digits. Roulette was notorious for not paying royalties to their artists who had to rely on their gigs for their income.

Today, EMI uses the "Roulette" name for the reissue of old Roulette label material. In the United States, Blue Note Records handles the Roulette jazz catalogue for release on the Roulette Jazz label.

Roulette Records artists
Alive N Kickin'
Pearl Bailey
Count Basie
Jimmy Bowen
Joanne Campbell
Cathy Carr
Marilyn Chambers
The Choir
Lou Christie
Dave "Baby" Cortez
Sammy Davis, Jr.
Joey Dee and the Starliters
The Detergents
The Devotions
Duane Eddy
Harry "Sweets" Edison
The Essex
Maynard Ferguson
Bill Haley & His Comets
Ronnie Hawkins
Tommy James
Tommy James & the Shondells
Buddy Knox
Frankie Lymon
Deidre McCalla
Lou Monte
The Playmates
The Rock-A-Teens
Jimmie Rodgers
The Three Degrees
Sarah Vaughan
Dinah Washington
Joe Williams
Anne Phillips
Eddie Palmieri "Harlem River Drive" album 1971