First SOUTHSIDE WITH YOU Trailer Enjoy the first SOUTHSIDE WITH YOU trailer! The film, written and directed by Richard Tanne, stars Parker Sawyers, and Tika Sumpter. SOUTHSIDE WITH YOU will be released in theaters on August 26. Chronicles the summer 1989 afternoon when the future President of the United States of America, Barack Obama, wooed his future First Lady on an epic first date across Chicago’s South Side.