"I missed the boat when I was doing Late Night"

This quote by Chris Elliott is likely describing his experience as a late night talk program host. He is revealing regret for not having actually taken advantage of the opportunity when it existed to him. He might be describing the reality that he was unable to profit from the success of other late night talk show hosts, such as Jay Leno, David Letterman, and Conan O'Brien. He may also be referring to the fact that he was unable to make a lasting impression on the late night talk reveal scene. By failing, he might have missed out on the possibility to go far for himself in the market. Ultimately, this quote is a reflection of his regret for not taking advantage of the chance when it was presented to him.