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In March 2011, Cassidy was cast in the ABC drama pilot Georgetown as Nikki, a smart and quick-witted junior staffer in the White House Communications Office with connections to the First Lady.

The pilot was created by Gossip Girl executive producers Josh Schwartz and Stephanie Savage. On July 23, 2016, it was announced that Cassidy had signed a deal with Warner Bros.

In June 2010, The CW announced Cassidy would have a major recurring arc in the fourth season of the teen drama series Gossip Girl.

Cassidy had her breakthrough in 2012, after being cast as Laurel Lance / Black Canary, on The CW television series Arrow.

Cassidy has reprised her role in the Arrowverse series The Flash and Legends of Tomorrow as well as voicing the character in the animated web series Vixen.

In 2017, Cassidy instead began playing Black Siren, an initially antagonistic version from a parallel universe, originating on The Flash and continuing on to Arrow. It's hard for me to even accept how old she is now." In 2003, Cassidy made her television and acting debut appearing in an episode of the Lifetime drama series The Division.

After Cassidy's parents ended their relationship, she was raised by her mother and stepfather Richard Benedon. Cassidy has continued to guest appear in television shows such as Celebrity Apprentice 4, Listen Up! In 2005, Cassidy appeared in a recurring role on The WB's series 7th Heaven over the course of four episodes.

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