In theater it's always nice to do different roles. Yet , I would say that there tends to be a "core" of shows that tend to be done a lot. By different theaters and groups. So the same shows sometimes "come around" more than a few times.

   I guess my question is this in a nutshell. There is a show I've done and a certain role in this show a few times. I was wondering if there were any thoughts on how many times is it appropriate to do a role in a show until it gets a bit "creepy". For instance... I know a person who has done a certain role at least 6 times in a show. Is that possibly "creepy"? Possibly too many?

Thoughts???

As long as you're still fresh in the role.  As long as it speaks to you.  As long as it has relevance for you.  Go ahead and do it.  Stop when it becomes mechanical, because at that point you're cheating yourself, your fellow actors, and your audiences.  (Unless, as it was pointed out, you're being paid for it; then do it because it's your job.)

I've only repeated one role; Grandpa in "You Can't Take It With You."  I did it as a senior in high school, then again 35 years later when I was more age appropriate.  I have directed a few individual shows two or three times, but most often with a ten year hiatus between productions.  But that's just personal choice.  There are so many things I still want to do, and the years are catching up with me.  No impetus, really, to duplicate anything.

Our theatre did Annie 10 years ago when I was 31.  I played Daddy Warbucks then and loved the role.  This year we did Annie again and once again I played Daddy Warbucks.  Rooster Hannigan and Drake also reprised their roles from ten years ago.  I think I have two more runs in me at 51 and 61.

Well.... admittedly I've done a certain role 3 times with 3 DIFFERENT theater groups who are physically more than 50 miles apart from each other. Basically I've worked with 3 completely different groups of actors and 3 different directors and I'm pretty sure that I've performed to three completely different audiences with not one person that I know having seen me more than once. I may be presumptuous but I'm pretty sure I got the role on three entirely different occasions with three different groups that I had no prior association because I was the best person to audition..... not because I was someones "friend" or I was familiar to the theater group. If I ever thought that was the reason I was getting a role I think it would be about time to put away the makeup, turn off the stage lights and find another hobby.
    

Possibly you could also do Mortimer. He says "I've been dying for forty years" at one point. He's probably "pretty old" too.

   But it's amazing that in the 5 page staging description at the beginning of the script of the "Fantasticks! written by the authors there is not one word referring to "Age" of characters. In the script.... only " sort of " to Louisa but that is not completely clear either.

   If you can portray the role.... my feeling is that age is unimportant.

But I guess the director can his or her own "age" bias. Be it right or wrong.