Bryson Tiller became one of the key breakout stars in 2010s contemporary R&B with the single "Don't" and a descriptively titled parent album, T R A P S O U L (2015), a moody swaggering set of slow jams that neologized a subgenre the singer/rapper took to the mainstream with multi-platinum certifications and Grammy nominations. True to Self (2017) and A N N I V E R S A R Y (2019), his subsequent studio albums, have either topped the Billboard 200 or reached the chart's Top Ten. Tiller's additional hits as a featured artist and duet partner are highlighted by DJ Khalid's "Wild Thoughts" and H.E.R.'s "Could've Been."
Featured appearances and non-album singles as a headliner led to the May 2017 release of Tiller's second album, True to Self. Another set dominated by thumping slow jams, it went straight to number one. Around the same time, Tiller was featured beside Rihanna on DJ Khaled's number two hit "Wild Thoughts." Additional featured appearances and other stray tracks preceded Tiller's third album. Most notable were duets with Jazmine Sullivan and H.E.R., respectively "Insecure" (for the soundtrack of the like-titled series) and the Grammy-nominated "Could've Been." Issued in October 2020, A N N I V E R S A R Y landed at number five and contained "Outta Time," featuring guest vocals by Drake and production from 40, Nineteen85, and Vinylz. A year later, coinciding with both Halloween and the tenth anniversary of his first mixtape, Tiller offered his second tape, Killer Instinct 2: The Nightmare Before. Another holiday-themed recording, A Different Christmas, was out the next month with Justin Bieber, Pentatonix, and Kiana Ledé on the guest list. The EP included mostly original songs and an update of "Winter Wonderland." In 2022, Tiller guested on Diddy's "Gotta Move On" and released the solo single "Outside."
