In 2005, Cummins performed at the New Faces showcase at the Just For Laughs Montreal Comedy Festival, catching the attention of both Comedy Central and The Late Late Show talent booker. In 2006, Cummins performed on Comedy Central’s Live at Gotham, his first performance recorded for television. A month later, he made his network television debut, performing on The Late Late Show with Craig Ferguson. Also, in 2006, he performed at his second major festival, the HBO Las Vegas Comedy Festival. The year 2007 started off with Cummins performing at the Comedy Central South Beach Comedy Festival, and then booking approximately 100 college dates at the NACA Nationals college booking convention in Nashville. Cummins then recorded his first television stand-up special, Comedy Central Presents Dan Cummins, in August at the Hudson Theater in New York. In 2008, Cummins performed at nearly 100 schools and also advanced to the semi-finals of Last Comic Standing, Season 6.