Jepsen released her debut single, a cover of John Denver’s song “Sunshine on My Shoulders”, in June 2008. Her debut album, Tug of War, was released in September 2008, and sold 10,000 copies in Canada. The singles “Tug of War” and “Bucket” peaked in the top 40 of the Canadian Hot 100, and received Gold certifications for sales of 40,000 units each. “Sour Candy”, a duet with Josh Ramsay of Marianas Trench was released as the final single. 2009, Jepsen toured western Canada with Marianas Trench and Shiloh.

2011, Jepsen recorded material for her second album with Josh Ramsay, Ryan Stewart, and Tavish Crow, her co-writer of “Call Me Maybe”. The track was released in September of that year. 2012, fellow Canadian pop singer Justin Bieber promoted the single on Twitter, and the next month, it was featured in a viral video in which Bieber, Selena Gomez, and Ashley Tisdale lip-synced and danced to it. Bieber’s manager, Scooter Braun, signed Jepsen to a joint worldwide record deal with his label, Schoolboy Records, and the major label Interscope Records. “Call Me Maybe” later peaked at number one on the Canadian Hot 100, making Jepsen the fourth Canadian artist to top the chart. In the United States, the single spent nine weeks at number one on the Billboard Hot 100, earning the title “Song of the Summer” from Billboard magazine. The single also topped the charts in 18 countries, including the United Kingdom, where it was the year’s second best-selling single. It was the best-selling single of 2012 worldwide, according to the International Federation of the Phonographic Industry (IFPI). The song was included on Jepsen’s six-track EP, Curiosity, released in February 2012 in Canada.

Following the success of “Call Me Maybe”, Jepsen recorded the duet “Good Time” with Owl City, released in June 2012. The song peaked at number eight on the Billboard Hot 100 and preceded Jepsen’s second album, Kiss, released in September 2012, and reached top ten chart positions in Australia, the UK, and the US. In Canada, the album is certified gold. The album also produced the singles “This Kiss” and “Tonight I’m Getting Over You”. 2012, Jepsen appeared on the fifth-season premiere episode of The CW primetime soap opera 90210, and became a spokesperson for clothing retailer Wet Seal.

Jepsen received the Rising Star Award at the 2012 Billboard Music Awards, the first Canadian recipient. At the 2013 Juno Awards, Kiss won the awards for Album of the Year and Pop Album of the Year. “Call Me Maybe” won in the Single of the Year category. The single also received nominations for Song of the Year and Best Pop Solo Performance at the 55th Annual Grammy Awards. In 2013, Jepsen became a spokesperson for clothing/footwear brand Candie’s. 2013, Kiss: The Remix, a compilation album containing remixes and instrumentals of singles from Kiss, was released in Japan, and peaked at number 157 on the Oricon albums chart. From June to October Jepsen embarked on The Summer Kiss Tour in North America and Asia. 2014, she performed in the Broadway production of Rodgers & Hammerstein’s Cinderella for 12 weeks. Later that year, Jepsen won the International Achievement Award at the SOCAN Awards, alongside co-writers Josh Ramsay and Tavish Crowe.

Jepsen was scheduled to perform at the Boy Scouts of America 2013 National Scout Jamboree, along with the band Train, but in March 2013, both cited the BSA policy on homosexuals as a barrier to their performance. Jepsen released a statement stating “As an artist who believes in equality for all people, I will not be participating in the Boy Scouts of America Jamboree this summer.”

Jepsen released her third album’s lead single, “I Really Like You”, in March 2015. Accompanied by a music video in which actor Tom Hanks lip-synced to the song, it peaked at number 14 in Canada and the top five in the UK. The album, titled Emotion, was released in June 2015 and received positive reviews; the album appeared on many publications’ year-end albums lists. Emotion became a cult favourite, attracting a more mature audience to her music. The album peaked at number eight in Canada and at number 16 on the US Billboard 200. It includes collaborations with Rostam Batmanglij (of Vampire Weekend), Sia, Dev Hynes, Greg Kurstin, and Ariel Rechtshaid. The second single, “Run Away with Me”, was released in July 2015. Later that year, Jepsen embarked on the Gimmie Love Tour in support of Emotion. Jepsen was also featured on a new version of Bleachers’ song “Shadow” from their album Terrible Thrills, Vol. 2 and released a cover of Wham!’s “Last Christmas”. Jepsen played Frenchy in Grease Live, Fox’s live television presentation of the musical Grease in January 2016. As part of her role, she performed a new song entitled “All I Need Is an Angel”. In late 2015, Jepsen recorded the theme song for the Netflix series Fuller House, a remake of the theme to Full House. In 2016, she appeared on The Knocks’ debut album 55.

Jepsen released Emotion: Side B in August 2016, an EP containing eight cut tracks from Emotion. The EP was listed on several end-of-year lists from publications such as Rolling Stone and Pitchfork. In May 2017, Jepsen released the single “Cut to the Feeling”. The song was originally intended for Emotion, but instead appeared in the animated film Ballerina, in which Jepsen voices a supporting role.

January and February 2018, Jepsen appeared as the opening act for Katy Perry’s Witness: The Tour. “Party for One”, the lead single from Jepsen’s upcoming fourth studio album, was released on November 1, 2018. Two more songs, “Now That I Found You” and “No Drug Like Me” followed on February 27, 2019. As of 2019, Braun was no longer Jepsen’s manager, although she was still signed to School Boy Records.

On May 21, 2020, the companion album Dedicated Side B was released, containing twelve outtakes from Dedicated. Following its release, Jepsen also confirmed the same month that she was making a “quarantine album” with songwriter Tavish Crowe with whom she wrote “Call Me Maybe”.