Season 1 1990 | 13 episodes The season 1 of The Outsiders aired from Mar 25, 1990. Cast (8) Jay R. Ferguson Ponyboy Curtis Rodney Harvey Soda Pop Curtis Boyd Kestner Darrel Curtis David Arquette Two Bit Mathews Robert Rusler Tim Shepherd Harold Pruett Steve Randle Kim Walker Cherry Valance Heather McComb Scout Jenkins Crew (2) Fred Roos Producer.he Francis Ford Coppola Producer.he Images Posters Similar Series Martín Rivas Youth