15. The Break-Up (2006) How could we not include a movie that’s literally titledThe Break-Up? In this better-than-expected film, Jennifer Aniston and Vince Vaughn star as a very modern American couple, whose flashy condo in Chicago becomes a battleground of the sexes. An art dealer and a tour guide, the two couldn’t be more different, hence their relentless bickering. Even when they’re just “roommates,” things are never smooth sailing for the pair....

15. Mahogany (1975) Diana Ross is known for being the lead singer of The Supremes, Motown’s best-selling girl group (and second best-selling girl group of all time right behind Spice Girls). What you might not know is that Diana Ross was an actress, too! And inMahogany, Ross stars as a fashion designer in Rome named Tracy Chambers, who has to start at the bottom of the ladder. Tracy doesn’t just design clothes; she models them....

15. On The Rocks (2020) On The Rocksis one of Sofia Coppola’s less dewy-looking movies in comparison toThe Virgin SuicidesorMarie Antoinette, but it still has that Coppola feminist essence. Laura (Rashida Jones) is a working novelist and mother in Manhattan, who could’ve turned out terrible given her misogynistic playboy father. Somehow, Bill Murray still makes the wealthy old white man likable (in his usual Bill Murray way). While catching up over olives and rocks, Laura’s father convinces her that her husband is cheating, mainly because he thinksallmen are “wired” to dominate women....

15. Road to Perdition (2002) Tom Hanks, Paul Newman, Daniel Craig, and Jude Law? Yes, please! Plus Oscar-winning director Sam Mendes? Don’t mind if we do! Road to Perditionwas the director’s follow-up to the highly successfulAmerican Beauty, and it didn’t disappoint. Hanks plays Michael Sullivan, a mob enforcer who’s running from the mob with his young son, who was witness to a hit. Fleeing through the 1930s American Midwest, Mike goes on more than one type of journey—discovering both himself and his connection to his son....

15. Mississippi Grind (2015) Gambling can be an intense, life-destroying addiction that’s as far from funny as it gets.Mississippi Grind, however, features Ryan Reynolds—so, obviously, it’s going to have laughs. His character ends up being incredibly good at gambling, all for one simple reason: he doesn’t care if he loses. On the other hand, Gerry (played by Ben Mendelsohn) does. The two meet at a casino in Iowa, and follow one drink with another, and another, and another…...