In 2009, Dan’s Comedy Central Presents was voted third favorite by fans in Comedy Central’s annual Standup Showdown. Shortly after, Comedy Central bought the rights to air a one-hour special. On October 17, 2009, in front of a sold-out audience at the Bing Crosby Theater in Spokane, Washington, Cummins recorded his first one-hour Comedy Central special, Crazy With A Capital F. Its initial showing on Comedy Central aired May 29, 2010. The accompanying CD was released on May 25, 2010; the DVD version was released on June 8, 2010.
Later in June 2009, Cummins performed at the second-annual Rooftop Comedy Aspen Comedy Festival. He made two additional television appearances in 2009, appearing on an episode of Byron Allen’s Comedy.TV, and on The Tonight Show with Conan O'Brien the day before Thanksgiving. The year 2009 also included the release of Cummins' first nationally distributed CD, Revenge is Near, on June 23 via Warner Brothers Records. It peaked at No. 7 on the Billboard Comedy Charts, and Punchlinemagazine.com put it in their top 10 list for the best comedy CDs of 2009.
Cummins has two children, a son and a daughter with his former wife, whom he divorced in 2009. Cummins shares custody of his children, who split time between Spokane, Washington and Coeur d'Alene, Idaho. Cummins married Lynze Radzyminski, a costume designer and wardrobe assistant, in August 2016.