10 Best Ryan Reynolds Performances

In the first early-to-mid-00s, Reynolds starred in a wide range of rom-coms, from Just Friends (2005) and The Proposal (2009), but none are as refreshing and well-crafted as Definitely, Maybe. Reynolds stars as Will Hayes, a political consultant who tries to help his daughter (Abigail Breslin) understand how he and her mother met, and why they're getting a divorce.

In his tale, Will talks about the three big romances in his life, and has his daughter try and guess which of them is her mother. With it's time-bending narrative and a great ensemble rounded out by Isla Fisher, Rachel Weisz and Elizabeth Banks, Reynolds is forced to balance the sadness of the film with the comedy, which is best explored during the scenes he shares with Breslin.

Reynolds is charismatic, sweet, affectionate, tragic and easy to root for, making every poor decision Will makes easy to forgive and understand. It's a tough line to walk, but Reynolds has no issues being the flawed leading man, and this film proves it.