1-MacGyver
2-Mickey Jagger
3-Doug Kenney and Robert Hoffman
4-Nimoy and Shatner
5-Stafford Repp aka Sgt O'Hara
6-Jack Nicholson and Anjelica Houston and Michelle Phillips
7-Lucas
8-Cast of Magnum, PI (Tom, John, Roger and Larry)
9-Sid Vicious
10-Siskel and Ebert
11-Spielberg
12-Phyllis Diller
13-X-Files cast
14-Jimi Hendrix
15-Weird Al
16-Dana Carvey and Phil Hartman
My final guess, I guess. I think Jack is with Anjelica and Michelle, two former girl friends. Always a dangerous situation but Jack survived.
Remember Jack, it isn't the years, it's the mileage.
How did I do?