How Justin Timberlake Accidentally Insulted a ’60s Legend to His Face originally appeared on Parade.
Justin Timberlake sure knew how to put his foot in his mouth as a young boy bander.
While visiting the set of Boy Meets World in the late ’90s, the former *NSYNC star, now 44, accidentally affronted another legendary boy band member, The Monkees’ singer and drummer Micky Dolenz, now 80.
Series stars Danielle Fishel, Will Friedle and Rider Strong recounted the awkward moment on the latest episode of their recap podcast, Pod Meets World. While discussing the Season 6 episode Bee True, Strong suddenly remembered that the “Bye Bye Bye” singers were on set that day, immediately leading Fishel to beg him to tell the story, admitting, “[It] cracks me up.”
Dolenz was present to direct, while his late bandmates, Peter Tork and Davy Jones, were featured in the episode. Timberlake, who would have been around 17 at the time, with the sixth season of the show airing from late 1998 to early 1999, was at the craft services table with Strong and Lance Bass.
The trio was chatting about what was coming up next for the group, with Timberlake telling Strong, “Well, they want us to do, like, a TV show—you know, like with the band acting.”
“I was like, ‘[Sigh], are you gonna do that?” Strong recalled. “Yeah, we really don’t wanna do that,” Timberlake replied, and the two “both just sort of acknowledg[ed] that’s kind of a crappy, cheesy, hokey idea.”
Unbeknownst to them, Dolenz, who was about 53 at the time (and had previously starred in the sitcom The Monkees from 1966 to 1968, the series that launched the short-lived band to fame), was right behind them.
“Micky Dolenz grabbed a handful of nuts right behind me from craft services and was like, ‘Why? Why not? Why not?’ and was just like, eating,” Strong continued, sharing the “Cry Me a River” singer’s stammering reaction. “And I just remember watching Justin turn, realize who he was talking to, make the calculation, and be like, ‘Ohhhh! Well, uh, it’s just not, you know, we’ll see, we’re on tour… we’ll probably—maybe, I mean, I don’t know why we wouldn’t.’ It was just one of the greatest moments…”
“You’ve got Justin Timberlake backpedaling in front of Mickey Dolenz of The Monkees,” Friedle laughed. “Only in Hollywood craft services tables you get to see this kind of stuff.”
“It’s a great moment,” Strong reiterated.
Related: Justin Timberlake Breaks Silence After Tour Criticism, Reveals Private Health Battle
How Justin Timberlake Accidentally Insulted a ’60s Legend to His Face first appeared on Parade on Aug 6, 2025
This story was originally reported by Parade on Aug 6, 2025, where it first appeared.
