Supernatural's Demon Dean will exercise his vocal chords during the season 10 premiere, and despite the hunter's terrible singing, he appears to be having quite the time.

Castiel Ready To Kill Demon Dean On 'Supernatural', Prepares Sam For Worst Outcome

New photos from the Supernatural season premiere show that Dean Winchester (Jensen Ackles) will live a carefree, no holds barred lifestyle now that he is a demon. Sam (Jared Padalecki), on the other hand, won't be enjoying his long, slow search for his missing brother.

The photos, which come from Oct. 7's "Black," show Dean taking on Atlanta Rhythm Section's Imaginary Lover during Karaoke night at the Black Spur Pub. Sporting a bit more hair than usual, Demon Dean can also be seen talking up a waitress while enjoying a drink. While Dean's morally ambiguous escapades may seem amusing, Ackles recently assured fans that is not the case.

Jensen Ackles On 'Difficult' 'Supernatural' Transition To Demon Dean, 'Womanizing Party Animal'

"There's nothing funny about this at all," Ackles said of Dean's new attitude, according to Spoiler TV. "He's so just kind of carefree and careless, [and] that I think is the scariest part about it to me, playing it."

Meanwhile, Sam will spend the premiere in hot pursuit of his previously dead brother. Unfortunately for Sammy, his search will lead him down some questionable paths and find him tied up at least once.

"Sam is so invested in finding his brother that it leads him to do some questionable things that will make him and, certainly, the audience wonder which one of these guys is the true monster," teased executive producer Jeremy Carver, according to TV Line.

Find out more when Supernatural returns to The CW on Oct. 7. Click the video below to see Sam and Dean's violent "Soul Survivor" (episode 3) reunion.

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