In 1999, he appeared in the controversial Catherine Breillat film Romance.

Siffredi is one of a few porn actors to enjoy crossover appeal and success with respect to other segments of the adult film industry, as well as some in mainstream media. Siffredi being interviewed by Rocco Tanica at Lucca Comics & Games 2016 the eyes going up from being surprised.' In mainstream media Speaking of his female partners, Siffredi says, 'I want to see emotion. will tell you that they have done things with him that they never do with anyone else.' Style of pornography ДЄctress Bobbi Starr noted of Siffredi, 'Any girl in the industry who has been with him. And I realised I don't want to lose my wife.' He later told the press, 'More than a year ago I started to get uncomfortable in the front of the camera.Something inside of me has changed.' However, he has continued performing sex in titles such as Rocco One on One and Rocco's Intimate Castings. I was all alone and it gave me a lot of time to think about what is important. He was reported to have told a friend, 'I never felt so naked as I did then. Despite renewed success, Siffredi announced his retirement once again in 2015, shortly after appearing on the Italian reality television show L'Isola dei Famosi ( Celebrity Island) which saw him stranded naked and alone on a beach for one week.

However, sexual frustration and disappointment as a director with his male talent and the state of the porn industry overall led Siffredi to return as a performer in 2009. Siffredi, while continuing to direct, was largely absent as an on-screen performer for nearly five years. He thought he found him in Nacho Vidal, but then Nacho went his own way'. 'My children are growing up,' he said, 'and I can no longer just say 'Dad is going to work to make money for the family.' They want to know more.' Regarding Siffredi's long career, Axel Braun commented, 'The problem is that he's been trying for years to find an 'heir to the throne', but it's no easy task. In June 2004, Siffredi declared that he would retire from performing in porn for the sake of his children, and instead focus on direction and production. Siffredi has credited Stagliano with being his mentor through all 30 years of his career. 'Rocco has far more power in this industry than any actress,' Stagliano commented in 2001.

Through collaboration with John Stagliano's Evil Angel studio and then his own Budapest-based Rocco Siffredi Produzioni as both a performer and director, Siffredi became one of the most powerful and recognizable personalities in pornography. However, it was Siffredi's performances involving anal sex and anilingus, as well as rough sex and his psychological intensity and athleticism, which earned him recognition and ultimately a cult following. Siffredi went on to perform in both plot-based and gonzo-style pornography, with styles of sex ranging from ordinary to extreme. Siffredi then stepped away from porn and worked as a fashion model, but returned to the business after two years with the help of porn actress Teresa Orlowski. ( Watch Out, Little Girls.) in 1987, in which he performed anal sex. Siffredi met porn actor Leonardo Codazzo in a French sex club in 1985 and was introduced to producer Marco and director Michela, who cast him in his first pornographic role, Attention fillettes.

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