A conservative lawyer named Diane takes her two teenage children Jake and Zoe to meet their estranged, hippie grandmother in Woodstock after her husband asks for a divorce.
| Actor | Role |
|---|---|
 Catherine KeenerDiane Hudson | Diane Hudson |
 Elizabeth OlsenZoe Hudson | Zoe Hudson |
 Nat WolffJake Hudson | Jake Hudson |
 Jane FondaGrace | Grace |
 Jeffrey Dean MorganJude | Jude |
 Chace CrawfordCole | Cole |
 Marissa O'DonnellTara | Tara |
 Kyle MacLachlanMark Hudson | Mark Hudson |
| JJoseph DunnRichard | Richard |
 Ann OsmondCindy | Cindy |
| TTeri GibsonElaine | Elaine |
| RRobert Bowen Jr.Robert | Robert |
 Wayne PyleParty Guest Man | Party Guest Man |
 Alison BallParty Guest Woman | Party Guest Woman |
 Joyce Van PattenMariam | Mariam |
| LLaurent RejtoThumbs-Up Cyclist | Thumbs-Up Cyclist |
| EEdward MorganFinger Driver | Finger Driver |
 Maddie CormanCarole | Carole |
 Denise BurseAngel | Angel |
 Poorna JagannathanMira | Mira |
| TTerry McKennaJasper | Jasper |
 Rosanna ArquetteDarcy | Darcy |
| KKai BeckTara's Friend | Tara's Friend |
 Katharine McPheeSara | Sara |
| DDana ChaifetzAstrologer | Astrologer |
| JJoe 'Jaz' ScaifariNude Biker | Nude Biker |
| AApril CrisafulliTara's Mom | Tara's Mom |
| MMichael Patrick BurkeFilm Festival Organizer | Film Festival Organizer |
| DDon StittCustomer | Customer |
 John FranchiCommuter (uncredited) | Commuter (uncredited) |