Bailey started acting in commercials at the age of two. Some national television commercials starring Bailey include, Clorox, Stouffer's, Juicy Juice, BMW, Bissell, and Mucinex. He guest starred in his first role, Strong Medicine in 2005 as Dougie Nauls. He co-starred in NBC's pilot Alpha Mom. He also starred in such television shows as Criminal Minds, How I Met Your Mother and Numb3rs.

In 2007, he joined the cast of Showtime/CBS serial-killer drama Dexter starring in a recurring role as Rita Morgan's son Cody Bennett/Morgan. He took over from Daniel Goldman from season one, playing the character in seasons two, three, four and five. He has appeared in a total of 34 episodes.

He has also starred in several films. Bailey was cast as Kate Beckinsale and David Schwimmer's son Timmy Armstrong in the feature film Nothing But the Truth. He co-stars in New Line Cinemas feature film Amusement which he filmed in Budapest, Hungary. He can also be seen in National Geographic / Paramount feature Arctic Tale starring Queen Latifah. Bailey was also cast to play the lead role of boy preacher Isaac Chroner in the TV remake of Children of the Corn. He starred in Cold Case in 2010. He has also starred in The Crazies as Nicholas Farnum.

Arctic Tale (2007)

Seven Years (2008)

Nothing But the Truth (2008)

Kay (2009)

Amusement (2009)

Children of the Corn (2009)

It's Always Sunny in Philadelphia (2009)

The Crazies (2010)

Eagleheart (2010)

Cold Case (2010)

Adalyn (2010)

Funny or Die Presents (2010)

Judy Moody and the Not Bummer Summer (2011)

The Apologist (2011)

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