Shortly after leaving law school, Martin started performing stand up in 1997. Four years later, in 2001, Martin caught his first big break in stand-up comedy when he appeared on Comedy Central's stand-up showcase Premium Blend. At the 2003 Edinburgh Festival Fringe he won the Perrier Award with his show If I. . . . The show was turned into a BBC television special in 2004. From 2003 to 2004, Martin wrote for Late Night with Conan O'Brien. In 2004, Martin had his own Comedy Central Presents stand-up special. His special was divided into three parts. In the first, he performed in traditional stand-up comedy fashion. In the second segment, he used humorous drawings as visual aids, which would serve either as the punchline or a background. During the third segment, he played a guitar and put on a pseudo-play where he would strum his guitar while alternating between playing harmonica and talking; some of his comedian friends dressed as fairies and dragons acted according to the story he was telling, detailing the magical land from where his jokes came. Martin's mother and grandmother also appeared.
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