This tutelage led to a significant improvement in their in-ring work. So much, that the Smoking Gunns became tag team champions just two years after debuting with the company. Gunn would eventually turn heel on Bart, and start a singles run as Rockabilly while being managed by the Honky Tonk Man. Billy stated that “[WWE] thought that they could get a little bit more out of me. It was a point where they were looking for more singles guys. It was nothing against Bart, but they just wanted to do a bit more with me.” Although he did break away to become a singles heel, his alliance with Honky Tonk Man was not a good as expected. “I think Honky was a little sour on the business, and just kinda wanted to get a paycheck. I don’t want to speak for him, but I just didn’t feel like me and him gelled too much together.”
One of the biggest moments in the history of DX was the invasion of WCW Nitro during their live show. When asked whether there was a plan if they were let in, Gunn stated, “There wasn’t any. Just get on this tank, drive down there, see what you guys can do. And if you get arrested, I’m coming to get you. It wasn’t like go try to get arrested, but just go push the boundaries and do whatever you could do. If they would’ve opened the door, we would have went in. The smartest thing Eric Bischoff could have done was to open the door and let us in. He’s got both companies on his TV show! We weren’t looking for fights, we weren’t looking for trouble. We just went down there to go down there, because at the time, that’s what DX did."
This led to one of the most controversial tag teams in WWE history–Billy and Chuck. “They had me off TV for a little while because they didn’t know what they were gonna do. They had Chuck not doing anything. So when I re-signed, and Chuck was there, they came up to us and was like, ‘Hey we want to do this thing were you guys are like male strippers and you want everything that the Divas want.’ It went from that, to what it became. When you look back, it was awesome. They needed ratings, and they needed something big to happen on that show, me and Chuck delivered. And it turned into us wanting a calendar, we want everything that the girls have, and it just slowly turned into we’re gonna be life partners and do the edgy kind of gay thing.“ He also explained that the biggest job for him was to play the character so well that it would be convincing to the audience, and “you always want to reach and play something that you think is a little bit out of your bounds, that you don’t think you could do, to challenge yourself a little bit more.” When asked who came up with the idea, he acknowledged Vince and Stephanie McMahon.
Gunn made an appearance at WrestleMania 31 along with other DX and nWo members during the match between Sting and Triple H. On the backstage plans of this interference, Gunn explained that it was the plan from the very beginning for both factions to appear at WrestleMania in opposing corners. “You’re really looking for moments. It is a Sting moment, because it’s the first WrestleMania he’s ever been in and he’s wrestling Hunter. But then again, from a company standpoint, how do we get the most out of this because our fanbase is not really a Sting fanbase? Sting being there is a big moment, but when you have DX and nWo behind that, it makes a little bigger in the majority of the people’s eyes. I’m not meaning to downplay Sting in any moment, but the way I look at it, it was just a bigger moment at a WrestleMania, rather than just that single moment.” When asked if he thought Triple H beating Sting was a good or bad idea, he responded, “I don’t know if I have an opinion either way. It could have went either way. I’m just up in the air about that. They all know a lot more than I do, so I just leave it up to them.”