“Valerie” by Amy Winehouse (Season Two, Episode Nine)
Since Santana did not become a series regular until season two, “Valerie” marks her first large solo performance. Although “Valerie” became Santana’s signature song throughout the show, this vivacious performance perfectly encapsulates Santana’s on-stage charisma.
“Landslide” by Fleetwood Mac (Season Two, Episode 15)
Guest star Gwyneth Platrow guides Santana and Brittany through this emotional ballad as Santana struggles with expressing her feelings to Brittany. Although the pair are not together at the time, this performance is a breakthrough for Santana, leading her to reveal her love for Brittany and finally come to terms with her sexuality.
In an interview with The Paley Center for Media in 2011, Rivera reflected on filming this scene with Stevie Nicks on set, noting that she knew she would remember the moment forever.