Alexander Stewart (born August 27, 1999, in Toronto, Ontario [1]) is a Canadian pop singer, songwriter, and social media creator known for his emotionally raw songwriting and massive online following. He rose to prominence with his singles "I Wish You Cheated" and "His Problem Instead," both of which charted on the Billboard Canadian Hot 100.[2]
Alexander Stewart | |
|---|---|
 | |
| Background information | |
| Born | August 27, 1999 Toronto, Ontario, Canada |
| Genres | Pop |
| Occupations | Singer, songwriter |
| Years active | 2018–present |
| Labels |
|
| Website | |
Stewart began his career as a teenager, uploading his first cover to YouTube in May 2013. His cover of Camila Cabello's "Havana" in 2017 became a breakout moment, propelling him toward original music and a growing fanbase.[3] Born in Toronto and now based in Los Angeles, he has described his catalog as a "sonic diary" — a public record of his life and emotions dating back to age 16.[4][5]
Stewart was the second-most popular artist on TikTok in Canada in 2023, and his platform presence has been a major driver of his success. His TikTok campaign for "I Wish You Cheated" amassed over 43 million views and led to a performance on The Tonight Show Starring Jimmy Fallon.[6] Across platforms, he has accumulated over half a billion streams globally, with hundreds of millions of YouTube views.[7]
His Juno-nominated debut studio album Bleeding Heart was released in May 2024. In November 2024, he reached number one on Billboard's Dance/Mix Show Airplay chart with "Wrong Way," a collaboration with LA-based producers Two Friends. His sophomore album, What If?, followed in October 2025, featuring singles including "Friends Don't" [8]with Lauren Spencer Smith, and was supported by a 34-date world tour.[3] Stewart also performed "The Way a Heart Breaks" on The Kelly Clarkson Show in October 2025 in support of the album.[9] In 2025, Stewart signed with Virgin Music.[10]
Early life
editCareer
edit2013–2018: Early days on YouTube
editStewart uploaded his first cover song to the YouTube channel Alec Stewart on May 24, 2013, performing "When I Was Your Man" by Bruno Mars.[12][non-primary source needed] His first official cover on his personal YouTube channel was New York State of Mind by Billy Joel. Over several years, he continued uploading cover songs to his YouTube channel, gaining popularity from his cover of Camila Cabello's "Havana", which he uploaded on October 22, 2017.[13] Following the song's popularity, he began writing and uploading his own songs.[14]
2019–present: Musical beginnings, Bleeding Heart, signing a record deal, What If?
editIn 2019, Stewart worked with Shaggy to release the single "You".[15]
On September 4, 2020, Stewart released his debut EP, Backwards, leading with the titular single, "Backwards", which reached #31 on Billboard's CHR/Top 40 radio chart.[16]
In May 2024, Stewart released his debut studio album Bleeding Heart.[17] It was preceded by the singles "Blame's on Me", "Broken by You" and the Billboard Canadian Hot 100 song "I Wish You Cheated".[18]
In August 2024, Stewart received an MTV Video Music Award nomination for Video for Good for his song "If You Only Knew".[19]
In November 2024, Stewart reached number one on Billboard's Dance/Mix Show Airplay chart with "Wrong Way" with L.A.-based producers Two Friends.[20]
In February 2025, Stewart received a Juno Award nomination for Breakthrough Artist or Group of the Year, and his debut studio album Bleeding Heart was nominated for a Juno Award for Pop Album of the Year.[21]
On June 12, 2025, Stewart announced on Instagram that he had signed a record deal with Virgin Music.[22][23]
On October 24, 2025, Stewart released his sophomore album, What If?,[24] which was preceded by singles "Blame On You",[25] "Here Again",[26] "Scared of Myself",[27] and "Friends Don't" with Lauren Spencer Smith.[28] Stewart is set to go on a 34-date tour to support the album, called the "What If? Tour", set to kick off in Manchester, United Kingdom on November 13, 2025, before coming to North America in early 2026, ending in Los Angeles, California on April 4, 2026.[29]
Discography
editStudio albums
edit| Title | Details |
|---|---|
| Bleeding Heart |
|
| What If? |
|
Extended plays
edit| Title | Details | Peak chart positions | ||||
|---|---|---|---|---|---|---|
| UK DL [30] | ||||||
| Backwards |
|
— | ||||
| Aftermath |
|
— | ||||
| If You Only Knew |
|
92 | ||||
| "—" denotes a recording that did not chart. | ||||||
Singles
editAs lead artist
edit| Title | Year | Peak chart positions | Certifications | Album/EP | |||
|---|---|---|---|---|---|---|---|
| CAN [31] | |||||||
| "Enamorado" | 2018 | — | Non-album single | ||||
| "Best Damn Thing" | — | Backwards | |||||
| "Backwards" | 2019 | — | |||||
| "Shy" | — | ||||||
| "Shady" | — | ||||||
| "No Thanks" | — | ||||||
| "This Is Your Life" | — | Non-album single | |||||
| "Single" | — | Backwards | |||||
| "Don't Give Your Heart Away for Christmas" | — | Non-album singles | |||||
| "Halo" | — | ||||||
| "Compare Myself" | 2020 | — | |||||
| "Stop & Go" (with Mime) |
2021 | — | |||||
| "House of Cards" | — | Aftermath | |||||
| "Let Me Hate You" | — | ||||||
| "24 Hours" | — | ||||||
| "Different People" (with Haven) |
— | Non-album singles | |||||
| "Echo" | 2022 | — | |||||
| "When You Love Someone" | — | ||||||
| "Back to You" | — | ||||||
| "Would You Lie" (with Seeb) |
— | ||||||
| "Blame's on Me" | — | Bleeding Heart | |||||
| "Leave Me in the Dark" | 2023 | — | Non-album singles | ||||
| "I'm Trying" | — | ||||||
| "Birthday Cake (Duet)" (with Dylan Conrique) |
— | Pieces | |||||
| "I Wish You Cheated" | 73 |
|
If You Only Knew and Bleeding Heart | ||||
| "He Never Will" | — | If You Only Knew | |||||
| "Broken by You" | 2024 | — | Bleeding Heart | ||||
| "Life at First Sight" | — | Non-album singles | |||||
| "Wrong Way" (with Two Friends) |
— | ||||||
| "Crossfire" (with Frank Walker) |
— | Origin (Deluxe) | |||||
| "Put You First" | — | Non-album singles | |||||
| "His Problem Instead" | 72 | ||||||
| "Here Again" | 2025 | — | What If? | ||||
| "Blame on You" | — | ||||||
| "Scared of Myself" | — | ||||||
| "Friends Don't" (with Lauren Spencer Smith) |
— | ||||||
| "Every Lifetime" | 2026 | — | Non-album single | ||||
| "—" denotes a recording that did not chart. | |||||||
As featured artist
edit| Title | Year | Album/EP | Ref. |
|---|---|---|---|
| "You" (Shaggy featuring Alexander Stewart) |
2019 | Wah Gwaan?! | [15] |
Guest appearances
edit| Title | Year | Other artist(s) | Album/EP |
|---|---|---|---|
| "Gone" | 2024 | Lost Frequencies | All Stand Together |
Tours
editAwards and nominations
edit| Award | Year[a] | Recipient(s) | Category | Result | Ref. |
|---|---|---|---|---|---|
| MTV Video Music Awards | 2024 | "If You Only Knew" | Video for Good | Nominated | |
| Juno Awards | 2025 | Himself | Breakthrough Artist or Group of the Year | ||
| Bleeding Heart | Pop Album of the Year |
- Notes
- ↑ Indicates the year of ceremony. Each year is linked to the article about the awards held that year, wherever possible.
References
edit- ↑ "Alexander Stewart on Apple Music". Apple Music. Retrieved March 25, 2026.
- ↑ "Alexander Stewart's "I Wish You Cheated" Is His First Canadian Hot 100 Hit". Billboard Canada. January 4, 2024. Retrieved March 25, 2026.
- 1 2 "Alexander Stewart Shares His Bleeding Heart". Rockshot Magazine. May 10, 2024. Retrieved March 25, 2026.
- ↑ "Alexander Stewart Interview". Euphoria Magazine. January 27, 2023. Retrieved March 25, 2026.
- ↑ "Alexander Stewart's Bleeding Heart". Beat Route Media. November 12, 2024. Retrieved March 25, 2026.
- ↑ "Alexander Stewart releases debut album 'bleeding heart'". The Noize. May 10, 2024. Retrieved March 25, 2026.
- ↑ "Rising TikTok Star Alexander Stewart Makes His Billboard Canadian Hot 100 Debut". Billboard. January 8, 2024. Retrieved March 25, 2026.
- ↑ "Alexander Stewart". First Avenue. Retrieved March 25, 2026.
- ↑ "Position Music Signs Alexander Stewart To A Global Publishing Deal". Music Connection. December 3, 2025. Retrieved March 25, 2026.
- ↑ "Alexander Stewart signs a record deal with Virgin Music". Melodic Magazine. June 13, 2025. Retrieved March 25, 2026.
- ↑ "Alexander Stewart". PopFiltr. October 14, 2023. Retrieved October 27, 2024.
- ↑ stewies family (May 2, 2021). "Alexander Stewart - When I Was Your Man (school concert, 8th grade)". YouTube. Retrieved October 28, 2024.
- ↑ https://www.youtube.com/watch?v=xKHFqmHzxmw
- ↑ Kuenzel, Antonia (January 27, 2023). "Alexander Stewart". Euphoria Magazine. Retrieved October 27, 2024.
- 1 2 Leiber, Sarah Jae (March 29, 2019). "Shaggy Released 'You' Featuring Alexander Stewart". BroadwayWorld. Retrieved October 27, 2024.
- ↑ Decter, Rosie Long (January 4, 2024). "Canadian Hot 100 First-Timers: Alexander Stewart Charts With "I Wish You Cheated"". Billboard Canada. Retrieved February 28, 2026.
- ↑ Gehlich, Clare (May 10, 2024). "Alexander Stewart shows his 'bleeding heart' in debut album". Melodic. Retrieved January 27, 2025.
- ↑ "Alexander Stewart releases debut album 'bleeding heart'". Noizemag. May 10, 2024. Retrieved January 27, 2025.
- 1 2 "2024 MTV VMA nominations: See the full list". ABC News. Archived from the original on September 7, 2024. Retrieved October 30, 2024.
- ↑ Cantor, Brian (November 3, 2024). "Two Friends & Alexander Stewart's "Wrong Way" Officially Reaches #1 At Dance Radio". Headline Planet. Retrieved September 23, 2025.
- 1 2 Siméon Dumont, "Les nominations des JUNOS 2025". Le Canal Auditif, February 11, 2025.
- ↑ https://www.instagram.com/p/DKzsWT6pfDe/?hl=en
- ↑ https://www.melodicmag.com/news/alexander-stewart-signs-a-record-deal-with-virgin-music/
- ↑ https://www.instagram.com/p/DN2yKFp2pf-/?hl=en
- ↑ https://www.instagram.com/p/DMIje0HRwhj/?hl=en
- ↑ https://www.instagram.com/p/DJ6-28jJBNT/?hl=en
- ↑ https://www.instagram.com/p/DOBcM4xjaEr/?hl=en
- ↑ https://www.instagram.com/p/DOgheQAjbjK/?hl=en
- ↑ https://www.melodicmag.com/news/alexander-stewart-reveals-the-what-if-world-tour/
- ↑ "UK Album Downloads Chart: 23-12-15". Official Charts Company. Retrieved October 28, 2024.
- ↑ "Canadian Hot 100: Week of January 13, 2024". Billboard. Retrieved October 28, 2024.
- "His Problem Instead": "Canadian Hot 100: Week of May 3, 2025". Billboard. Retrieved April 29, 2025.
- 1 2 "Canadian certifications – Alexander Stewart". Music Canada. Retrieved October 28, 2024.
- ↑ "Alexander Stewart". First Avenue. Retrieved October 28, 2024.
- ↑ "Alexander Stewart Announces the Bleeding Hearts Tour". Live Nation Entertainment. February 27, 2024. Retrieved October 27, 2024.
- ↑ Dunn, Mariah (September 24, 2024). "Alexander Stewart announces 'The Homecoming Tour' across Canada this fall". Melodic. Retrieved October 27, 2024.
- ↑ Ine, Joseph (July 29, 2025). "Alexander Stewart announces Here Again Tour in UK and Europe". Melodic. Retrieved August 10, 2025.
- ↑ Franzo, Allyson (October 26, 2025). "Alexander Stewart reveals the 'What If?' world tour". Melodic. Retrieved October 28, 2025.