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Vince Vaughn as Gary Grobowski
Jennifer Aniston as Brooke Meyers
Joey Lauren Adams as Maddie
Cole Hauser as Lupus Grobowski
Jon Favreau as Johnny O
Jason Bateman as Riggleman
Judy Davis as Marilyn Dean
Justin Long as Christopher
Ivan Sergei as Carson Wigham
John Michael Higgins as Richard Meyers
Ann-Margret as Wendy Meyers
Vernon Vaughn as Howard Meyers
Vincent D'Onofrio as Dennis Grobowski
Gary (Vince Vaughn) and Brooke (Jennifer Aniston) have been together in their relationship long enough to reach that point where familiarity and comfortability are starting to breed contempt, and they're going to have to reach some sort of understanding of compromise, or fall apart. Based on the title, it's not hard to figure out which way they choose.
It's a decent comedy trying to deal somewhat maturely with the complexities of relationships, particularly their ending. It's hampered by formulaic characters and situations which are good for a quick laugh but don't add depth to the various problems facing relationships. Relationships are long struggles, and rarely successful, and "The Break-Up" tries to show some of the truth of that, but isn't particularly interested in depth, which makes it all seem like a bit of a dodge, dressed up to seem like something more real than it is.
Gary is a typical guy - works hard, likes sports, his local bar, his PlayStation, and doesn't care for much else, or want to care. He's selfish and self-absorbed. He has his good qualities, or so other characters say, but they're not often on display. The film is hurt in that instance by the fact that most of the relationship has already taken place. Sometimes it's hard to see quite what Brooke sees in him. Brooke wants what a lot of people want out of a relationship - simple consideration - but makes the typical mistake of viewing her relationship in the context of a game. Neither one of them entirely approach their problems in a mature manner so it's no wonder things keep getting worse for them.
They are assisted fairly well by a strong supporting cast and the film's strongest scenes tend to be the ones using all of them, but as characters they tend to be a bit pointless. Like most modern comedies, "The Break-Up" is built around situation comedy; the supporting cast are there to make the situations work, and nothing else.
"The Break-Up" is a funny and light comedy, but it tries to be something a bit more without being something a bit more, hampered by shoddy characterization, ending up a bit empty.