Shailene Woodley...Amy Juergens (57 episodes, 2008-2010) Mark Derwin...George Juergens (57 episodes, 2008-2010) India Eisley...Ashley Juergens (57 episodes, 2008-2010) Megan Park...Grace Bowman (57 episodes, 2008-2010) Ken Baumann...Ben Boykewich (57 episodes, 2008-2010) Molly Ringwald...Anne Juergens (57 episodes, 2008-2010) Daren Kagasoff...Ricky Underwood (57 episodes, 2008-2010) Francia Raisa...Adrian Lee (57 episodes, 2008-2010) Greg Finley...Jack Pappas (56 episodes, 2008-2010) Renee Olstead...Madison Cooperstein / ... (50 episodes, 2008-2010)Luke Zimmerman...Tom Bowman (49 episodes, 2008-2010)Camille Winbush...Lauren Treacy / ... (48 episodes, 2008-2010)Steve Schirripa...Leo Boykewich (47 episodes, 2008-2010) Allen Evangelista...Henry Miller (46 episodes, 2008-2010) Amy Rider...Alic