On January 10, 2007, Kyle Cease announced on his official Myspace blog that he would begin shooting a one hour stand-up special for Comedy Central, due to positive response from his Comedy Central Presents. On March 15, 2007, Cease announced the special would be titled Weirder, Blacker, Dimpler. Filming was completed on March 30 in Seattle, Washington at the Moore Theater in downtown Seattle.
In 2009, Kyle was ranked #1 on Comedy Central's Standup Showdown. In June 2011 at the Longevity Now Conference, Kyle described how he was able to win the competition in spite of being up against comedic legends. Kyle decided to host a podcast and at the end of each episode, he thanked every fan who voted for him by name. On the first day, 400 people voted and Kyle thanked every single person. Each subsequent day, Kyle thanked every fan who voted. He attributes this to his success as it helped cultivate a substantial word of mouth following.