After a lengthy hiatus, The Boondocks is back, and Woodcrest is about to get a whole lot more crowded – and complicated. Season 5 introduces a new dynamic to the Freeman household with the arrival of Robert Freeman's new wife, Jennifer Winfrey-Freeman, and her son, Elias. While Huey grapples with newfound allies and Riley continues his quest for street cred, Robert struggles to adjust to married life and the challenges of raising a stepson who's anything but ordinary.