Later, as part of the rap group Almighty RSO with DJ Jeff 2X, Tony Rhome, and Antonio 2G, Benzino released a single “One In Tha Chamba” on Tommy Boy records and later signed with Rap A Lot records. His second crew, Made Men released the critically acclaimed Classic Limited Edition on Restless records in 1999.
Doomsday marked the end of the Almighty RSO, after which point Benzino formed the group Made Men (himself, Antonio Twice Thou, and Mr. Gzus) and the production team Hangmen 3 (himself, Jeff Two Times, and Johnny Bananas, the team had technically made their debut on Doomsday). Made Men debuted in 1998 on Restless Records with the single "Is It You? (Déjà Vu)," featuring Master P, and they also were featured on DJ Clue?'s The Professional (1998) shortly thereafter, with "Made Men." The full-length album Classic Limited Edition (1999) followed, along with a second single, "Just You and I." Whereas the Almighty RSO had been a group effort, Made Men was clearly a Benzino-helmed project: he was credited as executive producer, co-produced many of the tracks with Hangmen 3, and opened the album with "Benzino's Thoughts (Interlude)." Classic Limited Edition was met with critical praise from some corners, most notably The Source, which awarded the album four and a half (out of five) "mics" -- a near-perfect rating. A Hangmen 3 album, No Skits, Vol. 1 (2000), was the next Benzino project unveiled, this one on Surrender Records; featuring a variety of Boston rappers from the Made Men and Wiseguys collectives, the album was highlighted by the song "Holla Back (Holla Boston)." As part of Hangmen 3, Benzino also earned credits on albums by Prodigy (producing the song "What U Rep" from H.N.I.C., 2000), Nas ("Stillmatic [The Intro]," Stillmatic, 2001), Cormega ("Verbal Graffiti," The True Meaning, 2002), and Raekwon ("Planet of the Apes," The Lex Diamond Story, 2003).
In 2007 Benzino attempted to reestablish his rap career with the release of The Antidote. The CD was released independently and featured the 1st 48, his new group. Sales have been lackluster with under 75,000 copies sold. Benzino also made his return to media, establishing the tabloid Hip Hop Weekly with Mays.