In the late 1970s, Freddy became a member of the Brooklyn-based graffiti group the Fabulous 5, known for painting the entire side of New York City Subway cars. Along with other Fabulous 5 member Lee Quiñones, under his direction they began to shift from street graffiti to transition into the art world and in 1979 they both exhibited in a prestigious gallery in Rome, Italy, Galleria LaMedusa. In 1980, he painted a subway train with cartoon style depictions of giant Campbell's Soup cans, after Andy Warhol.
Freddy became a regular guest on Glenn O'Brien's public access cable show TV Party. As a frequent attendant at the Mudd Club and a participant in seminal The Times Square Show, Freddy was a bridge between the New York uptown graffiti and early rap scene and the downtown No Wave art scene. "I was bringing the whole music, hip-hop, art, break dancing, and urban cultural thing to the downtown table", he said.
In late 1980, Glenn O'Brien cast Freddy, along with fellow Lower East Side graffiti writer Quiñones, in the film New York Beat (later released as Downtown 81). The film showcased artist Jean-Michel Basquiat in his Lower Manhattan environment and the culture that surrounded it. Blondie lead singer Debbie Harry also appeared in the film and in early 1981, Freddy made a cameo in the Blondie music video for "Rapture." As recounted in the 1999 TV documentary The Hip Hop Years, the "Rapture" video featured Freddy in a cameo role painting graffiti art in the background. (Grandmaster Flash, who was also name-checked in the song, did not show up on the day of the shoot, so Basquiat took his place behind the turntables). "Rapture" was the first hip hop video to be shown on MTV.

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