Riley played Charlie Hogan, one of his best-known roles, in the 1986 film Stand by Me, and also received notice for his portrayal of Dave Frazier in the 1987 comedy Summer School.

He made notable appearances as a thief who steals money from Steve Martin's character's wallet in Planes, Trains, and Automobiles and as a naive metalhead customer whom Ken Kessler (portrayed by Judge Reinhold) cannot bear to rip off after discovering his girlfriend is pregnant in Ruthless People.

He also made guest appearances on such TV shows as Knots Landing, Growing Pains, a special hour-long episode of Amazing Stories directed by Steven Spielberg, and Airwolf.

[citation needed] As the 1980s came to a close, he spent much of his time following the Grateful Dead and later Phil Lesh and Friends.

[4] In addition, Riley has been a frequent guest of the "Adventure Club Podcast"[5] on ACPN, with hosts Guy Hutchinson and John J. Galbo.