It’s not a huge surprise that Orlando Jones would pitch some kind of TV event that would involve him interacting with Supernatural.
Oddly enough, Jones has become a huge fan of the CW series, often live-tweeting episodes and interacting with other fans.
In fact, he even started the Twitter hashtag #SuperSleepy in 2013 to come up with ideas for a Sleepy Hollow/Supernatural event, and has made appearances for the show’s fan conventions.
Jones has always seemed to favor the angel Castiel over either of the Winchester brothers, so it makes sense that he’d seize any opportunity for a crossover with Cas.