Cubby O’Brien was born in July of 1946 to a drummer and a housewife. His legal name is Carl Patrick O’Brien, but his mother thought he looked like a bear cub when he was an infant and gave him the nickname Cubby. This nickname suited him perfectly, and he has used it all his life.
Cubby is the third son of his parents, and he has two older brothers named Haskell O’Brien, Jr (after their dad) and Warren O’Brien. Haskell is a trumpet player and Warren followed their dad into a career as a drummer. Cubby’s dad, Haskell “Hack” O’Brien, was a well-known drummer at the time Cubby was born and played with several big band groups, which were popular at that time in history.
Cubby was born in Burbank, California, and grew up in Los Angeles, in a suburb called Shadow Hills, located between Sun Valley and Sunland. Cubby studied music at the Carl Babcock School of Music at five and excelled as a drummer. He later performed with the Roger Babcock Dixieland Band at local charity events and on local TV. After his time on The Mickey Mouse Club, Cubby attended the Hollywood Professional School, which he graduated from in 1962 as the president of his class.
Of course, Cubby is best known for being one of the original Mouseketeers on The Mickey Mouse Club. Like Annette Funicello, Cubby was chosen personally by Walt Disney to audition for the show. A Walt’s staff member had told him about Cubby and his talent after seeing him perform on the drums at a charity event in the spring of 1955.
Walt liked Cubby and cast him on the show. Despite having had little experience in singing or dancing before being on the show, Cubby was put on the first-string “Red Team” from the very beginning of it. It turned out that he was a natural at dancing and learned dance moves quickly enough to soon be able to perform in the show’s musical numbers. Cubby also had solo performances on the show but mostly centered on his drum-playing talent. Cubby stayed with the show for all three seasons and went on a live performance tour of Australia with some of the other Mouseketeers for a couple of years after the show was done.
After his time with the Disney Company, Cubby went to work for the Lawrence Welk company for two years. While with Lawrence Welk, Cubby performed with the show’s “Little Band” and did guest bits on the maestro’s show. Cubby also had a few small guest roles on other TV shows.
After graduating high school, Cubby had a significant amount of performing experience, and he began touring with Spike Jones, where he played show tunes and dance music with what became Spike’s last musical group. Also, Cubby played for Ann-Margaret on her live shows. In the late 1960s, Cubby occasionally played the drums on camera on The Carol Burnett Show on the CBS network.
Later, as he matured and gained even more performing experience, Cubby was the musical director for the Los Angeles touring companies of the Broadway shows Hair and Oh, Calcutta! This was in the early 1970s. He also performed for touring Broadway shows as a drummer during this time.
In 1973, Cubby began playing drums for the musical group The Carpenters as their touring drummer. He performed in this role until the early 1980s. Other drummers, and occasionally Karen Carpenter herself, played the drums on the group’s recordings, but Cubby played them for their live performances. Cubby and Karen Carpenter shared a love of the drums and other percussion instruments, and Cubby was able to introduce Karen to a big band drummer of some fame named Buddy Rich.
In the mid-1970s, Cubby appeared as a contestant on a TV game show on the ABC network called The Big Showdown. On the episode he appeared on, Cubby won $5,000 after rolling “Show Down” during the timed dice roll round of the show.
Cubby joined with his fellow former Mouseketeers in 1980 for a TV special. On this special, he sang, danced, and played the drums. In the early 1980s, he joined with some of these fellow Mouseketeers to do live shows on fall weekends at Disneyland.
Beginning in the 1980s and continuing to the present day, Cubby’s career has primarily involved performing as a drummer and human performer on Broadway shows and on live shows by well-known Broadway performers like Bernadette Peters. He lived in New York City for many years but has since moved back to Los Angeles.
As for his personal life, Cubby has been married three times. His first wife was Marilyn Miller, whom he met while touring with Spike Jones. They married in 1966, had one daughter, and divorced in 1976. Cubby’s second marriage was in 1978 to Terry Wilemon, who he met in Las Vegas when he was touring with The Carpenters. They divorced in 1999. Cubby’s third marriage was in 2002 to Holly Sims, who was, at the time, a flight attendant who lived in Portland, Oregon.
Cubby’s drumming activities keep him too busy to make a lot of personal appearances, but he does manage them occasionally. He lives in the Pacific Northwest and enjoys his Broadway career. His daughter Alicia married a TV director and writer named Tom Kramer, and the couple lives together in La Quinta, California.
Though he is seventy-four years old at the time of this writing, Cubby maintains an active career as a drummer, which is his first love as a performer. In this, he is following in the sort of “family business” started by his dad, which his brother Warren also followed him into. One of the most well-known Mouseketeers, Cubby maintains a fond place in the memories of the original and later fans of The Mickey Mouse Club.