Suggestions by @wickedtheatrefan

Cat Valentine

as Everyone's Baby Sibling in Sort by Tropes

Goomer

as Dumbass Has a Point in Sort by Tropes

Hudson Gimble

as Dumbass Has a Point in Sort by Tropes

Cat Valentine

as Dumbass Has a Point in Sort by Tropes

Jade West

as Death Glare in Sort by Tropes

Gabriella Montez

as Both Sides Have a Point in Sort by Tropes

Sharpay Evans

as Both Sides Have a Point in Sort by Tropes

Jade West

as Always Someone Better in Sort by Tropes

Sharpay Evans

as Always Someone Better in Sort by Tropes

Mercedes Jones

as Always Second Best in Sort by Tropes

Maya Hart

as Always Second Best in Sort by Tropes

Ennui

as Lana Del Ray in Character’s Favorite Artists Headcanon

Ferb Fletcher

as Coldplay in Character’s Favorite Artists Headcanon

Johnny (Sing)

as Coldplay in Character’s Favorite Artists Headcanon

Bethany Pearson

as Ke$ha in Character’s Favorite Artists Headcanon

Brittany Pierce

as Ke$ha in Character’s Favorite Artists Headcanon

Jade West

as Paramore in Character’s Favorite Artists Headcanon

Bridget (Descendants: Rise of Red)

as Charli XCX in Character’s Favorite Artists Headcanon

Ennui

as Billie Eilish in Character’s Favorite Artists Headcanon

Dez Wade

as Justin Bieber in Character’s Favorite Artists Headcanon