- 2009: Re-teamed with Abigail Breslin for "My Sister's Keeper," a Nick Cassavetes-directed adaptation of the Jodi Picoult novel
- 2008: Cast opposite Abigail Breslin in the family film, "Kit Kittredge: An American Girl"
- 2007: Once again played on-screen siblings with real life brother John in "The Martian Child"
- 2006: Co-starred with Frances McDormand, Jennifer Aniston and Catherine Keener in Nicole Holofcener's "Friends with Money"
- 2005: Voiced Abby Mallard (aka Ugly Duckling) in the animated feature "Chicken Little"
- 2004: Cast as Kate Hudson's sister in the comedy "Raising Helen"
- 2003: Played a prep school's straight-laced principal opposite Jack Black in the Richard Linklater directed "School of Rock"
- 2001: Starred as a Chicago high school teacher in ABC's "What About Joan"
- 2000: Had a small role in Stephen Frears' "High Fidelity" starring her brother John
- 1999: Voiced a yodeling cowgirl named Jessie, in the animated film "Toy Story 2"
- 1999: Played Hazel Huffman in the Tim Robbins-directed "Cradle Will Rock"
- 1997: Played Kevin Kline's bride-to-be whose life hinges on whether he is gay or not in the comedy "In & Out"; garnered second Best Supporting Actress Oscar nomination
- 1997: Once again co-starred with brother John playing his secretary in the comedy "Grosse Pointe Blank"
- 1995: Had a supporting role in the comedy, "Nine Months"
- 1994: Had a rare dramatic TV role in "The Mother" (PBS) opposite Anne Bancroft
- 1993: Played a murderous nanny in "Addams Family Values"
- 1989: Appeared Off-Broadway in the Circle Repertory Company's "Brilliant Traces"
- 1989: Played on-screen siblings with real life brother John Cusack in Cameron Crowe's "Say Anything"
- 1989: Earned a Best Supporting Actress Oscar nomination for her role as Melanie Griffith's best friend in "Working Girl"
- 1988: Made Off-Broadway debut in "Road"
- 1985: Series regular debut, NBC's "Saturday Night Live"
- 1984: TV-movie debut, "All Together Now"
- 1983: First appearance alongside brother John in "Class"
- 1980: Screen acting debut in "My Bodyguard"; her father also had small role
- While in college joined The Ark, improvisational comedy group




