After co-founding the record label XO, he released three mixtapes—House of Balloons, Thursday, and Echoes of Silence—in 2011, and gained recognition for his blend of contemporary and alternative R&B, as well as the mystery surrounding his identity.

He has earned seven diamond-certifications from the Recording Industry Association of America (RIAA) for his singles, and is the first artist to simultaneously hold the top three spots on the Hot R&B/Hip-Hop Songs chart.

[5][6] The only child of Ethiopian immigrants Makkonen Tesfaye and Samrawit Hailu,[b] who separated shortly after his birth,[8][9] he was raised in the suburb of Scarborough by his mother and grandmother.

[31] In 2011, Tesfaye met music executives Wassim "Sal" Slaiby and Amir "Cash" Esmailian, with whom, along with Taylor, he founded the XO record label.

[52] The album debuted at number four on the US Billboard 200 with first-week sales of 86,000 copies,[53] and has received platinum certifications from the Recording Industry Association of America (RIAA) and double-platinum from Music Canada.

[80] During the 2015 MTV Video Music Awards, Apple debuted a two-part promotional commercial featuring Tesfaye, which had a guest appearance from John Travolta.

[104] In September 2016, Tesfaye announced that his third studio album, Starboy, would be released on November 25, and included collaborations with now-disbanded French electronic music duo Daft Punk.

[179] Over 2021, Tesfaye reissued his three mixtapes in its authentic form with the original mixes and samples to celebrate the tenth anniversary of their release, with House of Balloons coming first in March 2021.

[196][197] Later that month, he appeared on Kanye West's tenth studio album Donda on the track "Hurricane", which won Best Melodic Rap Performance at the 64th Annual Grammy Awards.

The Hollywood Reporter stated that the series confirms the allegations that "Instead of subtly skewering the misogynistic and predatory nature of the business, The Idol became a forbidden love story — the stuff of a toxic man's fantasy", and called it "regressive rather than transgressive".

Originally intended as a soundtrack album, each EP was released following the premiere of each episode of the show, which featured collaborations with Future, Playboi Carti, Madonna, Lil Baby, Lily-Rose Depp, and Jennie from the South Korean girl group Blackpink.

[251] He has also cited Lana Del Rey,[252] David Bowie,[253] the Smiths, Bad Brains, Talking Heads, DeBarge,[254] 50 Cent, Wu-Tang Clan,[255][256] and Eminem as influences and inspirations.

[8] Hermione Hoby of The Guardian characterizes Tesfaye's songs as "narcotised-slow jams" and delineates their message as "partying is an existential experience, sex is fraught with alienation, and everything registers as unreal and unsettling.

"[264] Anupa Mistry of the Toronto Standard observes throughout his mixtapes a "cast of supine, stoned zombie-women... whose legs willingly part after being plied with substances and who morph into threats only when [he is] coming down and feeling vulnerable.

"[274] Tesfaye's first three mixtapes; House of Balloons, Thursday and Echoes of Silence, are alternative R&B projects that draw on dream pop, post-punk and trip hop, amongst others.

[282][283] In December 2015, Tesfaye was sued by Cutting Edge Music, which alleged that the bassline for "The Hills" had been taken from a composition featured in the score for the 2013 science fiction film The Machine.

In August 2019, the lawsuit was dismissed via summary judgment with the option to amend, with the court ruling that they had failed to show that Tesfaye or anyone else involved in making "A Lonely Night" had access to their song or that the works were substantially similar.

[289][290] In February 2020, Tesfaye and Kendrick Lamar were sued by the now-defunct indie band Yeasayer, claiming that "Pray for Me" includes an unauthorized sample of their song "Sunrise".

[292] In September 2021, Tesfaye, Nicolás Jaar, and Frank Dukes were sued for copyright infringement by producers Suniel Fox and Henry Strange, protesting that "Call Out My Name" is "strikingly [or] substantially similar, if not identical" to their 2015 track "Vibeking".

[299] In response to the allegations, Tesfaye mocked the reporting on his Twitter account, posting a clip of the characters in the show discussing the magazine saying, "Rolling Stone?

[302] In an interview with Vanity Fair, he continued to dismiss the reporting, saying that logistical difficulties with Seimetz's schedule and production timelines, as well as a desire not to rush his first show, propelled the overhaul.

[306] On March 7, 2020, during his third appearance as a musical guest on Saturday Night Live, he starred in the skit "On The Couch" with actors Kenan Thompson and Chris Redd.

[327] In April 2019, Tesfaye became an owner and global ambassador of the esports company OverActive Media, who owns the Splyce and Overwatch League team Toronto Defiant.

[334] After being presented with a Bikila Award for Professional Excellence in 2014, Tesfaye donated CA$50,000 to the University of Toronto to fund a new course on Ge'ez, the classic language of Ethiopia.

He was inspired to support the center after learning of French Montana's work with Global Citizen and Mama Hope to help raise awareness for Suubi and the people of Uganda.

[341] In August 2016, Tesfaye donated US$250,000 to the Black Lives Matter Global Network Foundation following numerous reports of police brutality in the United States.

[342][338][343] In May 2020, in response to the murder of George Floyd and the protests that followed, Tesfaye donated US$500,000 to the Black Lives Matter Global Network Foundation, Colin Kaepernick's Know Your Rights Camp, and the National Bail Out.

[354][355] On April 4, 2021, Tesfaye announced a US$1,000,000 donation through the United Nations World Food Programme (WFP) to relief efforts in Ethiopia for people affected by the Tigray War.

[398] In October 2014, Tesfaye was awarded the Allan Slaight Honour by Canada's Walk of Fame for "making a positive impact in the fields of music, film, literature, visual or performing arts, sports, innovation or philanthropy".

[399] Toronto mayor John Tory announced that the city would observe February 7, 2021, as the Weeknd Day to commemorate Tesfaye's Super Bowl halftime performance.