* "Crazy/U Drive Me Crazy" (Duet: Santana Lopez as Britney Spears and Rachel Berry as Madonna)
* "Stronger" (Performed by Rachel Berry)
Season 2:
* "...Baby One More Time" (Performed by Brittany Pierce)
Season 4:
* "Everytime" (Duet: Santana Lopez as Britney Spears and Sebastian Smythe as Michael Jackson)
Season 5:
* "Hold It Against Me" (Performed by Unique Adams)
* "Oops!... I Did It Again" (Performed by Mercedes Jones)
Season 6:
* "Work Bitch" (Performed by the Warblers)