Shortly, thereafter, he was cast starring opposite Helen Hunt in the CBS movie-of-the-week Murder in New Hampshire: The Pamela Wojas Smart Story and he then went on to appear on a number of other television shows including Lost, Party of Five, Chicago Hope and numerous others.

Concurrently, Jaymes produced and directed a number of commercials and web campaigns for companies such as Intel, Harper/Collins, Nikki Six, and LiveBooks.com, while also focusing his efforts on a myriad of Non-Profit Organizations, including One Generation and Island Dolphin Care.

Jaymes published a book, entitled Boxing Day about his experiences working in the 2004 tsunami disaster relief efforts[7] In 2010, Chris Jaymes co-wrote and directed Making A Scene starring William Shatner, Dave Foley, and Jason Priestley, a one-hour comedy for television,[4] which led to a string of shows for the CBC including Long Story Short a scripted comedy with Martin Short starring Robin Duke, Anne Murray, and Norman Jewison, and two pilots, including Late Night with Lang & O'Leary, and an entertainment news show, The Feed.

[4][8] In 2011, he directed the feature-length thriller, The Cottage starring David Arquette, Kristen Dalton, and Lorraine Nicholson, while also working with Levendis Entertainment and Nick Lambrou, developing the screenplay for the feature film action epic, Sons of Chaos, surrounding the Greek War for Independence.

During this period, Jaymes also worked closely with Jordan Beckett on various writing projects and participated as the piano player in the band Bootstraps, which was signed briefly to Capitol Records Harvest Label.

[9][10][11][12] Jaymes's screenplay Unconditional based on Joe Hoagland and the story that inspired the inception of Island Dolphin Care was recognized as a 2016 Semi-Finalist in the Academy of Motion Picture Arts & Sciences Nicholl Fellowship.

(2018 TV series) as Bryan, a recovered alcoholic trying to make his life right, as well as, starring in Constellations the award-winning two-hander play by British playwright Nick Payne directed by Kevin Keaveney.