Artists with the most #1 hits in Billboard Hot 100 history: 1⃣ The Beatles (20) 2⃣ Mariah Carey (19) 3⃣ Rihanna (14)..................... :) 4⃣ Michael Jackson (13) 5⃣ Drake (12) 5⃣ Madonna (12) 5⃣ The Supremes (12) 6⃣ Whitney Houston (11) 7⃣ Janet Jackson (10) 7⃣Stevie Wonder (10)