1. The Blues Brothers (1980)
From its depiction of the bustling, late ’70s Maxwell Street flea market to a climactic chase sequence that winds through Lower Wacker Drive to Daley Plaza, The Blues Brothers is a loving homage to John Belushi’s hometown. The film’s soundtrack reaches beyond the city’s limits, including tracks by Ray Charles, Aretha Franklin and James Brown, who also appear in cameo roles. Jake and Elwood’s journey takes them many places throughout the rollicking musical comedy, but the vivid portrait of the pair’s “Sweet Home Chicago” is what makes it memorable.