His 1991 song, "Good Vibrations," went gold. He became known for his antics on stage, where to the delight of screaming girls he dropped his pants.
"It's not like I should take credit for this ingenious idea. I just pulled down my pants. And my mother did not like it all," Wahlberg said.
When his mother complained, he told his mom he wouldn't do it anymore.
"And then you went out, and did it again," Logan pointed out.
"Yeah," Wahlberg admitted.
The dropping of his drawers inspired an ad campaign that featured Wahlberg in his Calvin Klein underwear.
"When you look back at that part of your career, how do you feel about it?" Logan asked.
"It was certainly, ah, got my foot in the door and allowed me to get where I am today. But I'm glad that I don't do that anymore," Wahlberg replied.
Soon after, Wahlberg received a pivotal phone call from director Penny Marshall. She was casting a new movie, "Renaissance Man."
"And when I sat down with her, I was like, 'Nah, I don't wanna act.' She goes, 'What do you mean? You're acting all the time, you're acting right now. You know, you're just acting like you're cool, you act like a tough guy. You know, take the pages. Go outside, look 'em over, and then come back in, and, and audition for one of the parts,'" Wahlberg remembered.
He did and he got the job.
"Was it hard for you to be taken seriously as an actor in the beginning? Did people kinda scoff at you because you were the sort of rap boy?" Logan asked.
"It was definitely something that was frowned upon. And I don't think all the other things that I was associated with helped. But you know I felt like really found my niche. This is what I'm supposed to be doing," Wahlberg said.
Acting forced him to become disciplined for the first time in his life. "In the music business, they kind of encourage you to be irresponsible," he said.
"You had been pretty good at being irresponsible up to that point," Logan pointed out.
"Exactly. So I needed the change of pace," he replied.
He earned the respect of critics after he pulled off a flawless performance as an innocent teenager turned porn star in "Boogie Nights."
"There's something so vulnerable about you in that film that really took people by surprise 'cause that wasn't the image that anyone had of you," Logan said.
"That was a big turning point for me, you know, 'cause I was really worried about 'What are the guys in the neighborhood gonna think?' But then I was, like, 'You know, what? If I wanna be an actor, I gotta be an actor. I can't worry about what everybody else's gonna think,'" Wahlberg explained.
A few years later came the film "The Departed" and an Oscar nomination for Wahlberg.
But what has perhaps given Wahlberg the most cachet in Hollywood is his series about Hollywood. As an executive producer, he developed "Entourage," the hit HBO show about a star actor who hires his boyhood friends to serve as his entourage.
Asked whose idea it was, Wahlberg said, "It depends on who you ask."
"I'm asking you," Logan replied.
"Well, obviously, I would say it's my idea because it's based on my life and my guys," Wahlberg said.
"It's based on your life, but how much of your life ends up in it?" she asked.
"Very loose," Wahlberg said.