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Sleepy Hollow was one of the most unexpectedly compelling shows on television when it debuted back in 2013, and Orlando Jones was a big part of why it was such a fun watch. Unfortunately for his fans, Jones left the show after Season 2 in 2015, and though he's moved on to other projects since, that doesn't mean he won't entertain thoughts of a return to the Sleepy Hollow universe. Orlando Jones shared this idea for a crossover between Sleepy Hollow and The CW's Supernatural:
I would do a Sleepy Hollow spinoff if you could get Misha Collins from Supernatural to team up, and we'd be demon exterminators together.
I can't say that I've ever thought about Orlando Jones' Sleepy Hollow police captain Frank Irving teaming up with Misha Collins' Castiel to fight the forces of evil together, but I'm on board. The two fan favorites on the same show at the same time could be pretty epic. Sure, Frank Irving is gone from Sleepy Hollow and Castiel is busy with angel issues on Supernatural, but stranger things than a crossover have come out of both series. Orlando Jones' Sleepy Hollow/Supernatural crossover pitch to TV Guide sounds like it could be awfully entertaining.
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.
Of course, Orlando Jones is pretty busy with other projects on the small screen. He landed a part in the Starz adaptation of American Gods, as well as a role in the upcoming BET series Madiba, since leaving Sleepy Hollow. Even if all the stars aligned between Fox and The CW for some kind of Supernatural/Sleepy Hollow event, it might be tricky to fit it into Jones' schedule.
That said, Supernatural shows no signs of stopping any time soon. It's currently the longest-running scripted series in The CW's history with twelve seasons, and it has already been renewed for Season 13. Frank Irving may not be returning to Sleepy Hollow, which returned for Season 4 with tons of big changes, but maybe Supernatural could find a way to bring him in for a demon hunt or or two with Castiel and the Winchester boys. Honestly, it would probably be one of the most awesome and least crazy things that Supernatural has done over the years.