Flynn wrestled for the World Wrestling Federation in June and July 1995. Flynn made appearances on WWF Monday Night Raw, WWF Wrestling Challenge and WWF Superstars of Wrestling, losing to WWF performers including Jean-Pierre LaFitte, Rad Radford, The Roadie and Waylon Mercy.
By 1996, Flynn had worked as a jobber for the WWF, performing in a few house shows before making his way into WCW. He began performing regularly on WCW's secondary television program, WCW Saturday Night, in 1997 and by the following year was gaining numerous wins over low-card performers.
In 1998, Flynn began to elevate his status, wrestling on Monday Nitro, the company's flagship program. He had a series of matches with Bill Goldberg, which saw Flynn come close to beating Goldberg, but ended up losing, adding several notches in Goldberg's streak. In 1999, he had a short-lived feud with Ernest "The Cat" Miller and his manager Sonny Onoo after Miller and Onoo attacked Flynn backstage during an interview with Gene Okerlund and cut off his hair. The feud ended when Flynn gained revenge by defeating Miller and Onoo in a handicap match at the Uncensored pay-per-view. Later that year, he unsuccessfully participated in the Junkyard Invitational at Bash at the Beach.
He then became a member of The First Family, a heel stable managed by Jimmy Hart. However, an injury Flynn sustained led to the eventual disestablishment of the group. He then began a feud with mixed martial arts fighter Tank Abbott. During this time, Flynn's persona emphasized his shootfighting skills including a "shootfight rules" match against The Wall on Thunder. His feud with Abbott culminated at the 2000 Souled Out pay-per-view, where Abbott defeated him via knock-out in a mere one minute, thirty-nine seconds. He was released in April of that year.