Richie gets escorted by beau Madden to a dinner date in Beverly Hills. Plus: George Clooney, Jim & Jenny and more

ROLE PLAY

George Clooney wears many helmets on the set of Leatherheads, filming Tuesday in South Carolina. PEOPLE's Sexiest Man both directs and acts in the 1920s-era football comedy, which also costars his former flame Renée Zellweger.