Tegan and Sara’s 15 Best Songs of All Time (Staff Picks)

After more than 20 years in the spotlight, queer indie pop duo Tegan and Sara Quin are taking a moment to reflect on their humble origins.

High School, the new Amazon Freevee television adaptation of the sisters’ 2019 memoir of the same name (out Friday), follows the lives of teenage Tegan and Sara (played by TikTok stars Railey and Seazynn Gilliland) as they come to grips with their sexualities, learn to live with one another, start their careers and survive the “universally sh–ty” experience of being teenagers, as Tegan told Billboard.

Not only is the show a fascinating look into life as a misunderstood teen in the ’90s; it’s a testament to the pair’s staying power as a musical duo. Their decade-spanning career has seen the Quin sisters take on whatever mantle best suited them in the moment, constantly adapting to the kind of art they were interested in making.

Look no further than the pair’s upcoming tenth studio album Crybaby, due out on Friday, Oct. 21 via Mom + Pop Records. The project blends elements of punk, pop and folk music to create yet another new sonic landscape that feels uniquely suited for Tegan and Sara

With their new show, a new record and years of experience under their belt, it would be only natural that the twins start thinking about their legacy as pioneering performers. Billboard is here to help in that exercise — below, Billboard staff members take a look back at the 15 songs (in no particular order) that best exemplify the breadth of work Tegan and Sara have given their fans since 1999.