Flynt's expansion into adult nightclubs, branded as Hustler Clubs, brought additional legal challenges. Several clubs faced zoning battles, community protests, and law enforcement raids alleging violations of obscenity or liquor laws. These disputes underscored how Hustler's brand extended beyond print, confronting local authorities who sought to regulate adult entertainment venues. Flynt's combative legal strategies and public relations campaigns often turned these conflicts into media spectacles. In one instance, he took on a small town mayor by holding an open audition for Hustler dancers at his club in that municipality. The contest attracted national attention and Flynt argued that it was protected under the First Amendment's right to free speech and expression. After several months of litigation, the city relented and allowed him to continue operating the club. Flynt also engaged in protracted legal battles with New York City officials after they denied a permit to operate a Hustler Club in Times Square. He responded by opening a temporary facility in defiance of the ruling, which led to a high profile showdown between him and Mayor Ed Koch. Eventually, Flynt won that case as well, but not before spending millions of dollars on legal fees. He later opened another Hustler Club in Las Vegas despite objections from casino magnate Steve Wynn, who claimed the club's adult content would tarnish the family-friendly image of his properties. Flynt again prevailed, arguing that the club met all legal requirements and could coexist with Wynn's resorts without harming them.
Despite these victories, Flynt remained embroiled in legal controversy throughout much of his career. His legal troubles continued when he expanded Hustler into other areas such as video production and adult retail stores. He faced multiple copyright infringement lawsuits over his use of copyrighted material in some Hustler videos, while others were accused of violating obscenity laws due to graphic sexual content. In one case, a federal jury awarded $50 million to a group of Texas police officers who alleged they had been fired for viewing pornography obtained from a Hustler store. Flynt appealed the verdict, claiming that it violated his First Amendment rights, but ultimately lost at both the state and Supreme Court levels. He also encountered trouble after launching an anti-religion campaign against evangelist Jerry Falwell, who sued Flynt for libel over a Hustler parody featuring himself having sex with his mother in an outhouse. The case was settled out of court for an undisclosed sum, which Flynt used to establish the First Amendment Project to defend free speech rights. Throughout these challenges, Flynt maintained his combative attitude towards authority and the media spotlight, often appearing on national television shows to discuss his legal battles and personal life.