New performance opportunities kept coming, including an offer from Just for Laughs.  Kevin turns to his manager Dave for advice, but it was thanks to Keith Robinson’s analysis of the opportunity that  Kevin realize the gaps and weakness that would make him lose his luster if he accepted the offer.

Keith, his mentor, became his father figure, advising and protecting him while his other friends see him and Torrei as “that couple ruining everyone’s night,” including their own. Keith finds the stories of the couple’s fights hilarious and he convinced Kevin to make them part of his set as a means to connect with his audience at a personal level. After a brief private rehearsal, Kevin had to face his fears and speak of himself. Though the laughter wasn’t heavy, it was heartfelt and made him realize he was the reason they came.

This shift in methodology earned him a meeting with Damon Dash, founder of Roc-A-Fella Records, who presents him with a movie opportunity. While he had been told that the movie was ready, he found out that he had to write it. However, Kevin felt that working with Roc-A-Fella artists was worthy of more than what he was paid, especially considering all the efforts he put in.  The move was a success though andDamon linked Kevin with a prospective TV show.

Excited about the amount he would make from the job, he informed his entire family. Unfortunately, the show gets canceled and this becomes his first major career disappointment. Despite a stellar show at the Montreal just for laughs, he missed the spot and learned about it from the selected finalist during drinks. But all the notoriety and his optimism worked in his favor as Dave managed to get him into the right meetings and with his charm, he earned himself a true Hollywood opportunity.