The year he turned 21, he released the mixtape House of Balloons and made his stage debut in Toronto. The year he turned 22, he played Coachella and released Trilogy, which debuted at No. 4 on the Billboard 200. The year he turned 23, Kiss Land debuted at No. 2 on the Billboard 200 and he opened dates on Justin Timberlake’s tour. The year he turned 24, “Love Me Harder,” a duet with Ariana Grande, reached No. 7 on the Hot 100.
The breakthrough yearThe year he turned 25, “Can’t Feel My Face” reached No. 1 on the Billboard Hot 100, his first No. 1 on the chart.
The year he turned 26, he won two Grammy Awards and released Starboy, which debuted at No. 1 on the Billboard 200. The year he turned 27, “Starboy” spent a week at No. 1 on the Hot 100. The year he turned 28, he released a surprise album that debuted at No. 1 and headlined Coachella for the first time. The year he turned 29, “Heartless” became his fourth No. 1 on the Hot 100.
The year he turned 30, After Hours debuted at No. 1 on the Billboard 200 and “Blinding Lights” reached No. 1 on the Hot 100. The year he turned 31, he played the Super Bowl halftime show, and “Blinding Lights” spent a record 88th week on the Hot 100.
The year he turned 32, Dawn FM debuted at No. 2 on the Billboard 200 and placed 24 songs on the Global 200 in one week. The year he turned 33, he became the first artist with 100 million monthly listeners on Spotify. The year he turned 34, “Timeless” with Playboi Carti opened at No. 3 on the Hot 100.
The year he turned 35, Hurry Up Tomorrow became his fifth No. 1 album and the After Hours Til Dawn tour passed $1 billion. The year he turned 36, Billboard reported the tour’s biggest month yet, $124.4 million in July.
The Weeknd released his debut mixtape in 2011, the year he turned 21, and reached No. 1 on the Billboard Hot 100 for the first time on Aug 10, 2015, the year he turned 25.
Ages are by calendar year (the year minus the birth year), birthdays aside.