Usher has notched over 50 appearances on the Billboard Hot 100 since “Thinking Of You,” off his self-titled 1994 debut, first charted. Those songs represent an ongoing temperature-check for the moods and styles of contemporary pop, from the guitar-flecked quiet storm of “Slow Jam” to the breezy Afrobeats of this week’s “Ruin.” It helps, of course, that throughout that timespan he did more than chase trends, arranging each of his albums around coherent themes and refusing to treat even deep-album cuts as anything less than essential. (Seriously: find the dud track on Confessions.)
Credit his voice, which simpers and emotes with fresh hurt when necessary but can punch as hard as a Max Martin beat when the chorus hits. Credit the dance moves, which hold their own alongside royalty like Beyonce and Michael Jackson. But mostly, credit his ear — the ability to find his pocket and stay contemporary over three decades of wildly fast-moving pop music. To celebrate his upcoming Super Bowl performance, here’s our ranking of his 25 best songs.