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Carl Patrick O'Brien was the youngest of three sons born to Haskell "Hack" O'Brien, a renowned professional drummer. His eldest brother, Haskell Junior, played trumpet, while the middle brother, Warren, was a drummer. Cubby earned his nickname from his mother, who thought he resembled a bear cub as a baby. The family resided in Sun Valley, California.
Cubby began seriously playing drums at age five while attending the Carl Babcock Music School in Sherman Oaks, where his father taught. By age eight, he performed multiple times with the Roger Babcock Dixieland Band on the Spade Cooley television show, as well as at rallies and benefits. One notable event was the 1954 Screen Actors Guild Christmas benefit, where a Disney producer noticed him and later informed Walt Disney. Walt then saw Cubby perform on the Ray Bolger Show and requested an audition for the Mickey Mouse Club.
Cubby was the only Mouseketeer musician permitted to play instruments on camera; whether this was due to Walt's casting choice is unclear. Unlike Annette, Cubby didn’t attract favoritism rumors, likely because his talent was evident. In the show's first week, he played drums during Talent Round-Up day alongside his father Hack and brother Warren. He was subsequently given numerous chances to perform rhythm instruments, but his abilities extended beyond music—he was a skilled comedic actor and learned enough dance to convincingly perform routines. His singing was decent, though he wasn’t featured for solos like Karen Pendleton.
In 1956, Cubby appeared in the Disney film Westward Ho, the Wagons alongside Tommy Cole, Karen, and Doreen Tracey. The four Mouseketeers had few lines and limited scenes in this lackluster Western. As the second season began, the show’s production numbers shifted focus to older teen couples. Cubby continued appearing in comedic segments, often solo rather than paired with Karen.
During the third season, Cubby introduced the serial The New Adventures of Spin & Marty and shared introduction duties for the Mousekartoon with Karen. These, like the Roll Call and Alma Mater segments that season, were single takes reused repeatedly. He also appeared in the Disneyland 4th Anniversary episode and was scheduled to play a part in the planned film Rainbow Road to Oz.
Similar to Annette, Cubby and Karen were offered contract extensions after the Mickey Mouse Club ceased filming, but the offer required both to accept. Karen’s father declined, leading to both being released along with the other Mouseketeers. Cubby immediately joined The Lawrence Welk Show, where he remained for two years. Coming from one close-knit studio family, he wasn’t ready to embrace another all-encompassing show family. After leaving, he led his own combo for a time while attending the Hollywood Professional School. He then toured for several years with Spike Jones, a dynamic bandleader and composer whose music defied categorization. Following that, Cubby worked with Ann Margaret, Jim Nabors, and The Carol Burnett Show, where Carol often engaged him in on-camera chats. While still with her show, Cubby also collaborated with Karen and Richard Carpenter and conducted for touring Broadway productions in the Los Angeles area.
Cubby met his first wife, Marilyn Miller, while touring with Spike Jones. They married around 1966 and had a daughter before divorcing approximately in 1976. In 1978, Cubby wed Terry Wilemon, but they divorced in 2000. His third marriage was in 2002 to a woman named Holly, with hopes that this union would last. Cubby continues working actively, drumming for various touring Broadway shows and performing with Bernadette Peters. He has participated in numerous Mouseketeer Reunion events, including the 50th Anniversary in 2005, though he is often too busy drumming to attend many personal appearances.
