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Bob Weir will be joined by Justin Bieber musical director/guitarist/jamband aficionado Dan Kanter at TRI Studios tomorrow evening for a very special #DanGetsWeird episode of Weir Here. It’s an interesting turn of events for sure—but it’s not the first time that Weir has found himself caught up in the world of teen pop idols. In honor of tomorrow night’s taping, we’re taking a look back at some of his greatest pop crossover moments.

Bob Weir Jams With Hanson

On February 13, 1999, Weir was joined by the boys of Hanson in the middle of his set with Rob Wasserman and Jay Lane for renditions of “All Along the Watchtower,” “Going Down the Road Feeling Bad,” “Wang Dang Doodle” and “One More Saturday Night.” It was the last show of a three-night run celebrating the tenth anniversary of 90s NYC jamband haven The Wetlands, and the collaboration was the brainchild of the club’s proprietor (and current Relix publisher) Peter Shapiro.Here’s an old school MTV News segment on the collaboration (the M used to stand for music, remember?)And here’s a recording of their take on “One More Saturday Night.” Taylor Hanson sounds pretty solid on the keys.Bob Weir and Mickey Hart Pay Tribute to America with Justin Timberlake and Lance Bass

On April 24, 2000 Bob Weir and Mickey Hart teamed up with the Saturday Night Live Band, Giovanni Hidalgo and more for a few tunes on the East Lawn in front of the U.S. Capitol Building in Washington, DC. The group was there to honor the 200th anniversary of the Library of Congress, and they were introduced by none other than Justin Timberlake and Lance Bass of boy band titans, N’SYNC. Weir, Hart and co. went on play “Aiko, Aiko,” “Truckin’” and “Fire on the Mountain” before joining Timberlake, Bass, Pete Seeger and more for a take on “This Land is Your Land.”

Bob Weir Takes a Photo with Justin Bieber*

We’re taking things a bit full circle with this one here. On July 23, 2010, Weir posted this photo on his Twitter account with the context-free caption “with @JustinBieber.” Little is known about the purpose of their encounter, but Bieber did post a tweet earlier on the same day that read, “BIG DAY today…excited. doing something new.”

We’re not sure if the two ever actually collaborated in any capacity beyond this photo—but who knows? Maybe a long lost Weir/Beiber bootleg will turn up on Furthur lot one of these days.

Bonus: Weir Covers Adele With His Daughter

Ok, so this isn’t exactly a teen pop star/Bob Weir collaboration but it’s kind of close. On May 28, 2011, Weir backed his daughter Monet on acoustic guitar as she sang Adele’s “Rolling In The Deep” during a benefit for the Ring Mountain Day School at Throckmorton Theatre in Mill Valley, CA.