O'Brien, like Annette Funicello, was personally selected to
audition for The Mickey Mouse Club by Walt Disney, in the spring of 1955.
Disney had been alerted to him by a staff member, who caught his live
performance at a charity gala.
Though he had little prior experience in singing or dancing,
O'Brien was placed on The Mickey Mouse Club's first-string "Red Team"
right from the start. He quickly picked up enough dance skills to perform in
musical numbers, though his solo performances remained centered around his
drums. He remained with the show for all three seasons (1955–1958) of original
programming, and after filming stopped, went on live-performance tours with
other Mouseketeers to Australia in 1959 and 1960.
Cubby was the only Mouseketeer allowed to play musical
instruments 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.
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