- One Sweet Day (Mariah Carey & Boyz II Men)
- Thriller (Michael Jackson)
- Poker Face (Lady GaGa)
- We Belong Together (Mariah Carey)
The answer here is actually One Sweet Day (surprised me too). The Hot 100 wasn't around for Thriller. Poker Face spent eight weeks at #1 and then nine weeks at #2, while We Belong Together is one of six songs to spent fourteen weeks at #1. But, its One Sweet Day by Mariah and Boyz II Men that spent a whopping and record-breaking sixteen weeks at #1.
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