Smothers Jr. had tried to break into show business for a long time. When he was younger, he was a reader of science fiction and collected comic books. According to Smothers, "If you looked at my interests on paper, you'd think you were looking at a guy who played Dungeons and Dragons." He took up music at the age of 14. In an interview, he stated "[...] as soon as I discovered KISS. I wanted to be a rock star." Smothers Jr. played in a rock band, and the group even made an appearance on a short-lived revival of the Smothers Brothers' television series. "I've been a musician for a long time. Primarily I'm a singer. It's a nightmare trying to get musicians together. It's like herding cats. If you can't pay them, forget it. You're lucky if they show up at all. I knew that if I was going to take a stab at having a career in entertainment, I was going to have to generate heat. [...] For me to light myself on fire for the world to see, I needed to douse myself in gasoline. Dick Smothers Jr. going out and releasing a CD of his music is not news. The closest you can get to breaking the law in the eyes of the public, without actually breaking the law, is to do porn."
Smothers Jr. made his pornographic acting debut in the Showtime softcore series My First Time. In 2003, he made his feature film debut in Bad Influence, a parody of The Graduate. His father, Dick Smothers, Sr., recounted in a 2003 interview that "My first reaction was, 'What name are you going to use?' ... He says he's going to use his name, and I said, 'Wait a minute. That's my name. I had it first.'" While Smothers, Sr. does not condone his son's career path, he does not condemn it either. "You look at someone who's been working hard at trying to make it for 21 years or so. This is the first acknowledgment of him being viable. Now he's really pleased that he's doing something that's causing me a lot of consternation. He's ringing my bell. It's 'Dad, I'm here, and like it or not, I'm not going away.' If that gets him somewhere, good. Fine. But I'm not going to make any judgments about it." According to Smothers Jr., "it didn't affect our relationship. We've never been the closest family."
Smothers Jr. has stated that he has no interest in participating in some of the more extreme aspects of the pornographic film industry such as gonzo films, and prefers to stick with couples-oriented productions, often films that make it onto cable television. He left penetration performance in 2004, on the day of the announcement of an AIDS scare within the porn industry. Since then, all lead roles taken by the actor have been performed with a stunt double for penetration sequences. Smothers Jr. has stated that he wants to work in other areas of the pornography industry in addition to acting. "What I really want to do is become the Orson Welles of porn, not only performing in these films, but writing, directing and doing the music." He currently lives in Santa Cruz, California.