Then: The tiniest boy Mouseketeer, Cubby O’Brien (in the bottom, middle of this group photo) won Mouse Club producers over with his advanced drumming skill. The 8-year-old had learned from his father, pro drummer Haskell “Hack” O’Brien, and he became the only Mouseketeer to play an instrument regularly on the show. He was so often paired with fellow 8-year-old Karen Pendleton on screen that for years, fans would believe the two eventually married in real life. “It just sort-of evolved because we were the two smallest,” Karen says. “They just thought we would look neat together,” Cubby says. A Red Team member from the start, he was also, with Karen, among the most popular Mouseketeers (aside from Annette Funicello, that is). The two, however, declined a joint contract offer to continue working for Disney — as a package deal — when the Mouse Club ended.

Now: After the show ended, Cubby (seen here at the Mouseketeers’ 50th reunion, on the far right) found immediate work for the next two years with the band on The Lawrence Welk Show. He’d spend the rest of his professional life as a working drummer. He played for Spike Jones in Vegas lounges at age 16 and with Ann-Margret’s Lake Tahoe act at 19. He served as musical director for a Los Angeles production of Hair and played with the band on The Carol Burnett Show. He toured with the Carpenters, Bernadette Peters, Andy Williams, Joel Grey, and Shirley MacLaine. He eventually moved to New York and found a more settled way to make a living in Broadway orchestras for the likes of The Producers and Gypsy. He’s now semi-retired in Oregon.

For more on the Mouseketeers’ lives on The Mickey Mouse Club and beyond, check out my book Why? Because We Still Like You.