3 Bizarre Collaborations That Somehow Worked Out

Most of the time, collaborations between musicians feel natural. A pop artist and a rap star. A rock outfit and a guest guitarist. Whatever the case may be, listeners aren’t often surprised by who an artist chooses to work with. However, there are times when the collaborations are completely unpredictable. Find three such duets–that worked out well–below.

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3 Bizarre Collaborations That Somehow Worked Out

1. “To All The Girls I’ve Loved Before” (Willie Nelson and Julio Iglesias)

On paper, Willie Nelson and Julio Iglesias don’t seem like perfect duet partners, but nevertheless their collaboration on “To All The Girls I’ve Loved Before” worked a treat. The song about past lovers earned them the top spot on the Hot Country Singles chart. The unique mix of their vocals was just odd enough to stand out.

To all the girls I’ve loved before
Who traveled in and out my door
I’m glad they came along
I dedicate this song
To all the girls I’ve loved before

To all the girls I once caressed
And may I say, I’ve held the best
For helping me to grow, I owe a lot, I know
To all the girls I’ve loved before

[RELATED: 6 Iconic Country Smashes That Turn 45 Years Old in 2025—From Dolly Parton to Willie Nelson, & More]

2. “Where the Wild Roses Grow” (Nick Cave and Kylie Minogue)

Kylie Minogue and Nick Cave joined forces for “Where the Wild Roses Grow” in 1995. Despite one artist being a pop princess and the other being a brooding indie artist, they hit a strong balance between both their strengths on this haunting track.

When he knocked on my door and entered the room
My trembling subsided in his sure embrace
He would be my first man, and with a careful hand
He wiped at the tears that ran down my face

They call me The Wild Rose
But my name was Elisa Day
Why they call me it, I do not know
For my name was Elisa Day

3. “The Lady Is a Tramp” (Tony Bennett and Lady Gaga)

Lady Gaga and Tony Bennett became close toward the end of the crooner’s life. Their many collaborations included this cover of “The Lady is a Tramp.” Their rendition of this jazz standard sounds as authentic as any that were released in the ’50s.

Doesn’t like crap games with barons or earls
Won’t go to Harlem in ermine and pearls
Won’t dish the dirt with the rest of the girls
That’s why the lady is a tramp

She likes the free, fresh wind in her hair, life without care
She’s broke and it’s oke’
Hates California, it’s cold and it’s damp
That’s why the lady is a tramp

Photo by Kevin Mazur for Getty Images