A charismatic jeweler (Adam Sandler) makes a high-stakes bet that could lead to the windfall of a lifetime. In a precarious high-wire act, he must balance business, family, and adversaries on all sides in pursuit of the ultimate win.

Petruchio is a poverty-stricken gentleman from Verona who journeys to Padua in search of a wealthy wife. There he meets Katharina, a self-willed shrew who leads Petruchio on a merry chase before he successfully circumvents her attempts to avoid marriage. After the honeymoon, Kate helps Petruchio win a wager that he has the most obedient wife. In reality, Kate has found a more effective way to dominate her mate.

After being dumped by his girlfriend, Matt sleeps with every girl he meets. Finally, Matt decides the only way to stop his sex obsession is to go 40 days and 40 nights living in a world of total abstinence. Then Matt meets Erica and the betting begins to see how long Matt can hold out.

Passepartout, a young, well-studied monkey, dreams of exploring the world, but his overprotective mother is intent on keeping him safe at home. When he crosses paths with the smooth-talking con-artist Phileas Frog, he finds himself caught up in a bet worth millions; to travel around the world in a record-setting 80 days.