He's made a lot of films, and many without the extreme age gaps, but some of them are rather
:
Manhattan(1979): 26 year age difference (Woody Allen, 43; Mariel Hemingway, 17)
The Curse of the Jade Scorpion (2001): 28 year age difference (Woody Allen, 66; Helen Hunt, 38)
Mighty Aphrodite (1995): 31 year age difference (Woody Allen, 58; Mira Sorvino, 27; Helena Bonham Carter, 29)
Everyone Says I Love You (1996): 30 year age difference (Woody Allen, 59; Julia Roberts, 29)
Hollywood Ending(2002): 34 year age difference (Debra Messing, 33; Woody Allen, 67) - He doesn't seem to have a problem casting himself opposite some of HW's most beautiful actresses either!
Whatever Works (2009): 41 year age difference (Larry David, 62; Evan Rachel Wood, 21)
You Will Meet a Tall Dark Stranger (2010): 39 year age difference (Anthony Hopkins, 72; Lucy Punch, 33)