I have recently finished writing a screenplay with a friend. It takes place in present day. Towards the end of the first act, we go to a flashback, 30 years earlier to 1978, when the main character was 8 years old. After the flashback, we come back to November of the next year.
So if the beginning of the film was in December 2008, we then cut to flashback in 1978, and come back to November of 2009. How would we label, or denote this? We were going to put TITLE OVER: November of the following year.
We felt that doing this might confuse people more, in thinking that it is just one year later than the flashback. We’re confused and want to make sure the reader isn’t confused.
It’s not clear from your example whether it’s important that the reader (and ultimately the viewer) know that it’s specifically 2008 — for instance, that it’s an election year. Most likely, it’s not important at all. The story is just set in “present day,” which happens to be 2008 or 2009. So I’d avoid any mention of the year except for the flashback, which is mostly to give a sense of relative ages and period setting.
Specifically, I’d recommend the following:
- Don’t say anything about the year until the flashback.
- Before that, if it’s important that it be December, give us a concrete visual (e.g. Christmas shopping) that lets us know the month, rather than a title over.
- For the flashback, don’t do a title over for the year. Just include  in the sluglines.
- When you return to the present, mark [PRESENT DAY] in the first slugline. You don’t need to continue it after that.
- If you need to show that 11 months have passed, give us a clear story indicator. Something or someone has grown or changed in the interim. (If nothing has changed, why are you jumping forward anyway?)
A project I’m currently writing moves forward a lot in time, much in the way The Godfather or Goodfellas does. At first, my instinct was to carefully label all the time cuts, but it quickly became clear that what mattered wasn’t the months but the forward progress of the story. Readers can keep up with you if they’re engaged.