[3] Osborne's directorial debut was the short film Feast (2014), about a Boston Terrier who loves getting fed junk food.

The short was produced by Walt Disney Animation Studios and premiered in front of Big Hero 6 (2014) in theaters.

Osborne had previously worked as an animator on films such as Wreck-It Ralph (2012) and Bolt (2008).

He directed Pearl for Google's Spotlight Stories, a short film about the relationship between a father and his daughter.

[citation needed] Osborne has been selected by Paramount Pictures and Weed Road to direct a film version of the video game Monument Valley, originally developed by Ustwo in 2015.