Original artist: R. Kelly
Who should have sung it: Artie
Why it would have worked: Take one infectious R & B song and add one wannabe ghetto white boy in a wheelchair and what do you get? Ridiculous perfection. Artie’s voice has just enough soul in it that he can pull these numbers off — think his Usher “Confessions” solo — and his glasses-clad, nerdy, girl-crazy persona makes his take on slightly sleazy songs like this one hilarious as well as genuinely pleasing to the ear.
‘I Won’t Say (I’m in Love)’
Original artist: Disney’s Hercules
Who should have sung it: Santana
Why it would have worked: Glee has featured exactly two Disney songs ever — “Bella Notte” and “Let It Go,” but, battles over song rights aside, we always wanted more. If Santana’s coming out story hadn’t been so tearful, and so intrinsically linked to her love for Brittany, this would have been a gorgeous number for our “straight-up bitch” falling for someone new, backed by the other New Directions girls as the Muses.
‘I Guess That’s Why They Call It The Blues’
Original artist: Elton John
Who should have sung it: Blaine
Why it would have worked: This would have been a perfect solo piano performance for Blaine: a big, raw, emotional number that we got to see the live take of on screen. Think the “Teenage Dream” reprise and “Against All Odds.” Like those songs, this one would have fit thematically somewhere in season 4 — maybe when Kurt and Blaine are struggling with a long distance relationship.
‘Son of a Preacher Man’
Original artist: Dusty Springfield
Who should have sung it: Unique
Why it would have worked: Come on. Have you ever HEARD this song? We don’t even need an excuse other than the idea of Unique doing this in any context is a gift that Glee deprived us of. Seriously, any context — a competition solo, a weekly assignment, hell, we’d even take a literal ‘Unique falls for the son of the local minister and needs to sing her feelings’ scenario. Just give the girl this song.
‘Brown Eyed Girl’
Original artist: Van Morrison
Who should have sung it: Puck
Why it would have worked: For a show that paid tribute to nearly every iconic musician in history, it’s shocking that Van Morrison never made it in. No “Moondance,” no “Gloria,” no “Have I Told You Lately.” These are some of the biggest songs of all time, but maybe none more so than the classic radio staple “Brown Eyed Girl.” Puck’s talent for blending rock and swing and giving it some extra charm make him the man for the job here.
Original artist: The Dresden Dolls
Who should have sung it: Tina
Why it would have worked: Occasionally, the show covered artists that Glee’s audience may consider obscure, like Black Kids, Hey Monday, The Waitresses and Lykke Li. The Dresden Dolls, with their goth cabaret aesthetic, make perfect sense as a personal choice of Tina’s, and this anthem about the power of song could have easily been swapped out with the My Chemical Romance number of the same name in “Comeback.”
‘Stand By Me’
Original artist: Ben E. King
Who should have sung it: Finn
Why it would have worked: Another iconic classic rock song that it’s hard to believe that Glee never used. This one could have only ever been for Finn. His voice might have lacked the richness of the original, but he would have put heart into it, and we would have loved him for it. We’re thinking original New Directions era, a weekly assignment choir room performance with some sort of sweet but heavy-handed lesson to be learnt.
‘I Knew You Were Trouble’
Original artist: Taylor Swift
Who should have sung it: Marley
Why it would have worked: Glee has done a couple of Taylor Swift songs, but nothing off of either Red or 1989, the albums that took her from country sensation to the world’s biggest pop star. It would have been fun to see “Shake It Off” make it into season 6, but the Glee character that most suits Tay vocally is probably Marley. This hit would have been a great fit for the ongoing mess that was her relationship with bad-boy Jake.
‘I Am What I Am’
Original artist: Broadway’s La Cage Aux Folles
Who should have sung it: Kurt
Why it would have worked: Although the number’s original context is about a drag queen, this song has become a defiant anthem for queerness, individuality and pride (lower and uppercase P) in general. “I Am What I Am” could have easily replaced “Rose’s Turn” in season 1 and delivered the same message, or it could have been used at countless other moments in Kurt’s life, either as a formal performance or a moment of self-expression.
Original artist: Frank Sinatra
Who should have sung it: Rachel
Why it would have worked: “My Way” is the ultimate retrospective number, about living life to the fullest. This unreleased Celine Dion version is exactly the right key and delivery for Rachel, and maybe if the Glee finale had done a Parks and Rec and showed us these characters a long way in the future, we would have seen a Rachel in the autumn of her years, belting this out one last time.