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The most obvious matchup didn't occur to me before, Jacob Wheeler's "Magic" with Mio's "Evergreen" (the other Gundam 0083 ending song), although the algorithm seems to strongly prefer "Evergreen" with "Magic" mostly being relegated to background noise.

If I'm mashing up things with Gundam OVA ending songs anyway, here's Megumi Shiina's "Distant Memory" (from Gundam 0080: A War in the Pocket) with Michael Jackson's "Heal the World", although it skips over the parts of both songs that I think most sound alike (the melody of the first line of each verse). Incidentally, the Gundam 0080 song predates the commercial release of "Heal the World" on the Dangerous album by around two-and-a-half years, though I suspect any similarity is coincidental.

And, speaking of Dangerous, here's the title track of the Michael Jackson album mixed up with the Roxette song of the same name.
 
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The Carpenters' "Top of the World" with ABBA's "Super Trouper"

What's the connection? Just that they're both non-Christmas songs that still sound Christmasy to me.

(I know Anni-Frid "Frida" Lyngstad is wearing what looks like a Christmas sweater during the verses of the "Super Trouper" video, but I don't think I ever saw the music video until I got the ABBA Definitive Collection DVD in 2002 and I thought the song had kind of a festive feel long before then.)
 
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"Same title, different song".

Jennifer Rush & Huey Lewis and the News: "The Power of Love"
(N.B. the Jennifer Rush "Power of Love" is the song that Celine Dion covered more famously but I'd rather use the original.)

Joe Jackson & Kool and the Gang: "Steppin' Out"
No idea why that one turned out so short.

Madonna & Kool and the Gang: "Cherish"
They're both beach-centered videos so at least the visuals kinda blend together even if the songs don't quite as much.

Elton John & Whigfield: "Saturday Night"
 
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