The 51-year-old founding member of '90s boy band NSYNC spoke to the 40-year-old Canadian television personality during a "No Strings Attached" interview. Chatting on her "Phone a Friend" podcast, Cruickshank revealed she was ecstatic to ask the star questions she's been "dying to know since I was a tween."
In the episode, titled "God Must Have Spent A Little More Time on Chris Kirkpatrick," the singer opened up about his time in the "Bye Bye Bye" boy band alongside Justin Timberlake, JC Chasez, Lance Bass and Joey Fatone.
In 1995, Kirkpatrick founded the boy band in Orlando, Florida, where the five-man group rose to superstardom. Over the course of four albums, NSYNC earned numerous accolades, including eight Grammy nominations and seven MTV Video Music Awards, until they went on an indefinite hiatus in 2002.
Since then, Kirkpatrick has experienced numerous opportunities. Even in the past few years, he has performed at the Coachella Valley Music and Arts Festival alongside Ariana Grande, appeared on reality TV shows like "The Masked Singer" and even earned a star on the Hollywood Walk of Fame with his bandmates.
But while talking to Cruickshank, the star revealed none of those once-in-a-lifetime opportunities beats his most-loved experience.
"I think about all of those, but my favourite is the family part," he shared on the podcast episode, which was posted on March 9. "Being a dad and getting to do that type of thing."
Kirkpatrick, who shares his five-year-old son Nash with wife Karly Skladany, added that having Nash witness the excitement in his life is also a benefit.
"Just to have him be around it and see. I don't know if he really understands, because I think he thinks most dads get to do fun things like that," he said. "And I'm sure in different ways it is, but it's odd for him if people come up or stop me and want a picture."
After NSYNC's members went their separate ways in 2002, Kirkpatrick said deciding on his next steps was "confusing," if anything.
"It was really difficult to go from being a poor kid in a trailer park, to starting a band, to getting to be in this huge band and then the band just stopping and not understanding a next step or where to go or what my next move should be," he admitted. "That's kind of where a lot of the partying and things that I got into happened. It wasn't a great thing, but it was the process of me learning and growing up and figuring out life."
He likened the band's temporary hiatus to people who take a semester off of university but never return because they end up committing to something else in life.
While Justin Timberlake had suggested the group take a break, Kirkpatrick clarified that the group's hiatus wasn't necessarily because Timberlake wanted a solo career. Instead, each member had their own interests to pursue.
The split also wasn't the result of any drama or competition with other reigning boy bands at the time; Kirkpatrick cleared the air about there being any potential "beef" or competition between the Backstreet Boys and NSYNC.
"For us, we were in competition with ourselves. We always looked at just trying to be better, trying to be better than the last show, trying to have a better record than the last record," he said. "Every single thing we did was, just try to be better than we were.
"When we started, [the Backstreet Boys] were already put together. ... We were always just a little behind them."
He added that Lou Pearlman, the record producer behind the two boy bands, and his colleagues made it clear that the Backstreet Boys were their "darlings" while NSYNC was the "red-headed step-child that was trying to take their spotlight."
Kirkpatrick continued to say that management "did try to put labels" on NSYNC's members but it was a "strange" concept since all the boy were similar.
"In no way was I anywhere near a 'bad boy.' I mean, other than tattoos or occasional — or a lot — of drinking and having fun in clubs. But we all kind of did that," he added. "All five of the guys, there's things about me and Joey that are exactly alike, there's things about me and J.C., J.C. and Joey, Justin and Lance. We all have similarities with each other."
When asked about his thoughts on a possible NSYNC reunion, Kirkpatrick noted that he was open to the idea, a notion that co-NSYNC star Lance Bass also recently shared.
"I wouldn't say 'absolutely,' but I also wouldn't say 'never,'" Kirkpatrick shared. "We're all still friends, we all still joke about things all the time. Who knows? It could happen, it may not happen. But in the end, we were a band of five brothers and [we] enjoyed everything we go to do.
"We know that we have great fans out there that would love for us to do something. I think it's a matter of all five of us figuring out a time when, 'You know what? Let's make the band a priority again.'"