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Killam made six guest appearances as Gary Blauman on his wife Cobie Smulders' TV series, How I Met Your Mother.
The sketch briefly became an Internet phenomenon and garnered Killam media and public attention.
His mother had toured with The Charlie Daniels Band, and has been described as a singer-songwriter; his father was a part of the City Garage Theatre Group, and is described as having had acting ambitions.
and after, the UCLA’s School of Theater, Film and Television "as a musical theater student", where he reports having "spent much of his time working on UCLA’s Theater Festival", and which he left "to pursue his acting career".
Killam co-starred in the 2013 comedy film The Heat.
Killam voices Zip "Frantic" Danger on the Hulu original series The Awesomes.
In 1994, Killam made his first film appearance as a young boy in Naked Gun 33⅓: The Final Insult.