In the wake of the hip-hop and R&B takeover that defined the mid-’00s in pop music, 2006 saw top 40 in something of a transitional space. Rap was still at the center of everything, but with superstars Kanye West and 50 Cent in between album cycles, OutKast starting to fracture and Eminem in self-imposed exile, it was left without a major centrifugal force — a void rap’s self-proclaimed King of the South stepped up to fill. And while R&B remained massive, it continued to merge with pop in unexpected ways, with the acoustic midtempo sound of Norwegian producers Stargate and the pen of rising songwriter Ne-Yo — starting to step into the solo spotlight himself — taking over radio, marking a major shift from the nu-soul and crunk-n-B that had dominated R&B earlier in the decade.

Swarming the top 40 landscape in 2006 came a wave of bands and solo artists — many boosted by synchs on new hospital drama Grey’s Anatomy, the hottest show on television — who attempted to offset turbulent times with mellow, comforting, piano-based pop-rock. Meanwhile, emo’s pop crossover continued, with its most-hyped new band even taking the top prize on MTV’s biggest night. Disney pop began to show itself as an undeniable (and growing) mainstream force. And the biggest hip-hop producer of the turn of the century brushed off the first cold streak of his career with a pair of projects that dramatically reinvented the pop stars behind them, leading to the biggest hits of their careers.

Billboard‘s 2006 Week, celebrating the artists, songs and trends that defined the music of that year, begins here with our staff’s picks for the best singles of the bunch — including songs that reached or topped the Billboard Hot 100 for the first time in 2006, but not ones that waited until future years to make or top the chart. Go ahead and let your hair down as we tell you our favorite songs from 20 years ago. (You can also see in each entry how the songs ranked in 2006’s chart-based Year-End Billboard Hot 100.)