MAJOR UPDATE
So with Indiana Jones and the Kingdom of the Crystal Skull coming out 19 years after the last one (The Last Crusade, 1989) the question turns to what are the longest periods between original and sequel or sequel and sequel. I created a lot of confusion with this (I have a talent for that kind of thing) so let me define more clearly. As I say in the comment section "Putting "International Velvet" and "The Black Bird" at number one, in my opinion, was wrong. When thinking of a sequel, a true sequel, we think of an actor reprising their role. I think "Texasville", "A Man and A Woman: 20 years Later", "Psycho II" and "The Color of Money" fit this bill and "International Velvet" and "The Black Bird" do not."
"Belle Toujours" also has an actor from the original reprising a role but not the lead, not Catherine Deneuve. Those other four have the main characters reprising their roles. Effie may be around in "The Black Bird" but Bogart is not."
5. Last Picture Show 1971 - Texasville 1990 (19 years)
4. A Man and A Woman 1966 - A Man and A Woman: 20 Years Later 1986 (20 years)
3. Psycho 1960 - Psycho II 1983 (23 years)
2. The Hustler 1961 - The Color of Money 1986 (25 years)
1. Alphaville 1965 - Germany Year Ninety Nine Zero 1991 (26 years) Submitted by Ed Howard.
Category Two: Longest time between continuing stories without the same leads.
3. (tie) National Velvet 1944 - International Velvet 1978 (34 years)
3. (tie) The Maltese Falcon 1941 - The Black Bird 1975 - with George Segal as Sam Spade's son and Lee Patrick reprising her role as Effie. No, I'm not kidding. (34 years)
2. Belle Toujours 2006 - Belle Du Jour 1967 (39 years) - submitted by JS.
1. Return to Oz 1985 - The Wizard of Oz 1939 (46 years) - submitted by par3182.
I'd include The Road to Tara too, but I'd rather submit theatrical releases only, not made for tv stuff. Thanks to everyone for the submissions. If anyone can think of any more that outdo these I'll update again. Let me know.