Josh Flagg Meets the Roaring Twenties 47 photos Next GalleryBefore They Were Agents: MDLLA 10555366 Josh steps out of his sweet ride with the help of his driver, Jeff, looking like he fell right out of roaring twenties. 10555371 This car could only be fit for one man. 10555376 Josh looks out dramatically into the distance. 10555381 He seems far too comfortable in this outfit. Have you done this before, Josh? 10555386 The smile of a man who knows he has a listing in the bag, thanks to an imaginative plan. 10555391 These two belong together. 10555396 Do you know anyone else who could pull this look off? We didn't think so. 10555401 We can't help but wonder what Josh's real estate career would be like in the 1920s. 10555406 Josh seems to have this pose down to a science. 10555411 He isn't just an impeccably dressed real estate agent, but a man who cares about the history of his hometown. 10555416 Any outfit can be pulled off if you have the confidence of Josh Flagg. 10555421 Bet you haven't seen a 1929 Durant...ever. 10555426 Josh and his assistant Hillary look completely prepared for this open house. Previous Pause Next 1 of 13