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Carl Patrick O'Brien was the youngest of three sons of Haskell "Hack" O'Brien, a well-known professional drummer. His oldest brother Haskell Junior played trumpet, while the middle brother Warren played drums. Cubby got his nickname from his mother, who thought he looked like a bear cub as an infant. The family lived in Sun Valley, California.
Cubby began playing drums in earnest at age five, while attending the Carl Babcock Music School in Sherman Oaks, where his father taught. At age eight, with the Roger Babcock Dixieland Band, Cubby performed several times on the Spade Cooley television show, and at rallies and benefits. One of these was the 1954 Screen Actors Guild Christmas benefit, where a Disney producer spotted him and later told Walt. Walt Disney then saw Cubby perform on the Ray Bolger Show and requested he be auditioned for the Mickey Mouse Club.
Cubby was the only musician among the Mouseketeers who was allowed to play on-camera; whether this had something to do with Walt casting him or not is unknown. Certainly Cubby never had the rumors of favoritism surrounding him like Annette did, possibly because his skill was obvious to all. In the show's first week, he got to play drums for Talent Round-Up day in a combo with his father Hack and brother Warren. From then on he was given many opportunities to play rhythm instruments, but his talent didn't end with music; he was a fine comedic actor, and learned enough dancing on the show to fake his way through the numbers. His singing was ok, though he wasn't called on for solos like Karen Pendleton.
Cubby appeared in the Disney film Westward Ho, the Wagons with Tommy Cole, Karen, and Doreen Tracey in 1956. The four Mouseketeers had barely any lines and very few scenes in this tepid Western. As the second season started, the Mouseketeer production numbers shifted more to emphasizing older teen couples. Cubby still appeared in comic bits, but he was more often solo than paired with Karen.
In the third year Cubby did the introductions for the serial The New Adventures of Spin & Marty, and shared introduction duties for the Mousekartoon with Karen. Like the Roll Call and Alma Mater for this season, these consisted of a single take used over and over. He also appeared in the Disneyland 4th Anniversary episode, and was slated to play a role in the proposed film, Rainbow Road to Oz.
Like Annette, Cubby and Karen had been offered a contract extension after the Mickey Mouse Club stopped filming, but the offer was contingent on both accepting. Karen's father decided not to accept the offer, so the pair were cut loose like the other Mouseketeers. Cubby went immediately to The Lawrence Welk Show, where he stayed two years. Having just come from one close studio family, he wasn't ready to accept another all-encompassing show family. After leaving that show, he had his own combo for awhile, while going to the Hollywood Professional School. He then toured for several years with Spike Jones, a manic bandleader and composer, whose music defies description. Cubby then had gigs with Ann Margaret, Jim Nabors, and The Carol Burnett Show, where Carol often chatted with him on camera. While still playing for her show, Cubby also began working with Karen and Richard Carpenter, and doing conducting for touring Broadway shows in the Los Angeles area.
Cubby met his first wife Marilyn Miller while touring with Spike Jones. They were married around 1966, and had a daughter together before divorcing around 1976. In 1978, Cubby married Terry Wilemon, but that too ended in divorce in 2000. He married for the third time in 2002, to a lady named Holly, and we'll hope the third time is the charm. Cubby still works constantly, playing drums for various touring Broadway shows, and with Bernadette Peters. He has taken part in many of the Mouseketeer Reunion shows, including the 50th Anniversary in 2005, but usually is too busy drumming to make personal appearances.
