In season one of ST, they played Sunglasses at night by Corey Hart and it did not come out until 1984.

I am watching Season 4 right now and on the first episode they played a song by Extreme that did not come out until 1989. Also I am watching Episode 2 of Season 4 right now and the scene of Steve and Robin in the video store talking about their love lives and Robin found their morning movie Doctor Zhivago and Steve says he does not do double VHS there is a copy of A Christmas Story that was released by MGM/UA Home Video in the mid-90s under their "Family Entertainment" banner.