Though he broke through as a brash teenager, Mac Miller evolved into one of the more thoughtful and surprising rappers of his era. Born Malcolm McCormick, the Pittsburgh native first emerged with such nostalgic boom-bap as 2010’s “Nikes on My Feet” and “Kool Aid & Frozen Pizza,” before 2011’s playful, party-ready Blue Slide Park became only the second independently distributed debut to top the Billboard 200. Even back then, his sensitive side came through on tracks like “Missed Calls,” which spun a melancholy melodic hook out of soft, phone-like tones. He embraced more rap on 2012’s “Loud” and circled back to his DIY roots on 2015’s “100 Grandkids,” while scoring his biggest hit to date with 2016’s “Weekend,” a soulful collab with Miguel. Teamups with Anderson .Paak (“Dang!”) and Ariana Grande (“My Favorite Part”) brought a more pop-friendly audience to his 2016 album The Divine Feminine, a triumph in splitting the difference between popular appeal and creative ambition. When his subject matter grew dark, addressing substance abuse and mental health on tracks like “Self Care,” he was candid and personable, channeling his struggles into relatable art. McCormick passed away in late 2018, aged 26, and his estate has since released two acclaimed posthumous albums—2020’s Circles and 2025’s Balloonerism—featuring singles such as “Blue World” and “Funny Papers,” respectively.