Angela Robinson made a short film D.E.B.S. in 2003 and then expanded it into a feature film in 2004. But only one actress, Jill Ritchie, reprised her role from the short.
I was thinking El Marachi becoming Desperado both made by Robert Rodriguez
Suicidal Tendencies’ “Still Cyco After All These Years” was a remake of their eponymous debut album (the original is far superior).
Whitesnake’s remake of “Here I Go Again” was a hit in 1987, and they later remade “Fool For Your Loving” with less spectacular results.
Iron Maiden re-recorded two songs from of their 1980 debut album in 1999 as b-sides.
For music, Loudon Wainwright III did an album called “Recovery,” which was a selection of songs from his first four albums that were rerecorded and reinterpreted 35 years later.