Regina Hall and Don Cheadle on Black Monday's chaotic will-they-won't-they romance

Black Monday’s first season was a tightly constructed doomsday clock of a dark comedy, counting down to the titular 1987 stock market crash and the mysterious death of one of its key players. Since then, the series has broken from that mold and wisely leaned into its stellar ensemble, following the nefarious—and highly entertaining—cast of characters wherever their greed takes them. At the start of season three, Don Cheadle’s Mo Monroe is running a small but successful music label, while Regina Hall’s Dawn Towner has been making the most of her prison sentence; in other words, their Wall Street days are in the past. But no matter how many times Black Monday turns the tables, its one constant is the on-again, off-again relationship between Mo and Dawn. Are they better as business partners, or romantic partners? Or perhaps they’re better off out of each other’s lives entirely? Ahead of the season three premiere on Showtime, The A.V. Club spoke with Cheadle and Hall about the cosmic push-and-pull of the pair, and whether or not they’re rooting for them to make it in the end. And, with Black Monday now entering the ‘90s, the stars discussed the slick fashions and terrible trends (looking at you, Columbia House CD Club) that defined the decade.

Black Monday’s third season premieres on Showtime on May 23.