Jack and Jill vs. the World

Jack (Prinze Jr.) is a thirty-something New York City advertising executive, living a life forged from routine. He is successful and stylish... and extremely bored. Jack meets Jill (Manning) by chance on a rooftop. Jill is looking for an apartment and asks Jack for directions. Jack suggests Jill's name for an ad shoot. Later he drives Jill to her apartment and realizes the neighborhood may not be all that safe. He helps Jill move out of her place and the two move in together by week's end. The pair pieces together a playful manifesto of "rules to live by." Jack's best friend and business partner, George (Stebbings), notices a more playful side to Jack's usual cynicism, and wants to meet the cause.

Jill's free-spirited nature causes some friction, however. When her long absences go unexplained, Jack forces Jill to confess that her disappearances are a result of the treatment she needs for cystic fibrosis, an ultimately terminal illness. Jack is furious with Jill for violating their pact of honesty, and they break up.

A talk with his father Norman (Forster) incites Jack to find Jill. Jack tracks down her wacky friend, Lucy (Parise), and pleads his case. Convinced that he truly loves Jill, Lucy admits that Jill is catching a Greyhound bus cross-country to Hollywood. Jack reevaluates his life, and just as he quits his job, a bomb threat is called in at his work. Jack goes outside and George tells him that the bomb threat was called in by someone who wants to fight ugliness. Jack realizes that the culprit has to be Jill. The two make up, and with their new dog in tow, they hit the highway... with no destination in sight except for a life together.

• Freddie Prinze Jr. as Jack
• Taryn Manning as Jill
• Robert Forster as Norman
• Vanessa Parise as Lucy
• Kelly Rowan as Kate
• Peter Stebbings as George
• Ingrid Doucet as Sally
• Lisa Ciara as Amberly
• Darrin Brown as T-Bone
• Claudia Besso as Melony
• Krista Sutton as Emily
• Julian Richings as Mr. Smith
• Ethan Penner as Wyatt
• Hannah Lochner as Holly
• Charles Martin Smith as Carlin

The film garnered a mixed reception from critics. According to Reel Film reviews it "ultimately establishes itself as an affable endeavor that benefits substantially from the charismatic work of its two leads."[1] But Robert Abele of the Los Angeles Times concluded that it is "Blind to the fact that it should be rising up against its own formulaic kind."[2]

The soundtrack features music by Canadian indie rock band Stars.

The DVD was released on June 14, 2008.

• Jack and Jill vs. the World at IMDb
• Jack and Jill vs. the World at Rotten Tomatoes
• Jack and Jill vs. the World at MySpace
• Official Website