In 1994, Cutlass used his own label, Hoody Records, to produce The Frankie Cutlass Show, from which his classic Hip Hop single "Puerto Rico" charted on the Top Hot Dance Billboard chart at number 42. In 1995, Cutlass released his second single "Boriquas on the Set" featuring Fat Joe, Doo Wop and Ray Boogie as an underground hip hop hit and peaked at number 29 on Billboard Hot Rap Songs. It would lead him to a recording deal with Relativity Records,Violator Records and Epic Records. By the mid-1990s, Cutlass became a member of the Funkmaster Flex team "The Flip Squad" and started spinning at special events, and on the airwaves for New York City's Hot 97 (WQHT) Radio Station. Frankie's interest had expanded into production as well as leading him to work with popular artists such as Notorious B.I.G, Uncle Luke, Fat Joe, Shaggy, Rayvon, Akinyele, Mad Lion and veteran Latin Music artists Tito Nieves. 1997 saw the release of his second album, Politics & Bullshit, paying tribute to old-school rap and featuring artists such as Redman, Busta Rhymes, Mobb Deep, Fat Joe, Smif-n-Wessun, Sadat X, Biz Markie, Craig G, Kool G Rap, M.O.P., Keith Murray, Heltah Skeltah, the Lost Boyz and Roxanne Shanté. The album charted on Billboard 200 albums at number 129, Billboard Top R&B/Hip-Hop albums at number 32 and Billboard Heatseekers albums at number 4.