22. Jermaine Dupri "Sweetheart" (1998)

Album: Life in 1472
Producer: Jermaine Dupri, Mariah Carey

"Sweetheart" never quite performed like one would have expected a Mariah Carey feature to perform in 1998, reaching only No 125 on the Billboard singles charts; it was initially planned as a single, but the record company pulled it at the last minute (although many singles still entered circulation). It qualified for Billboard due to rule changes that took effect that fall, allowing album tracks to chart through airplay.

Drawn from Jermaine Dupri's solo debut Life in 1472, the song featured such an incredible Mariah performance that she managed to make Dupri seem like a guest on his own song. Today, the song's low-key groove and impeccable vocals make the label's decision surrounding the single even more mysterious.

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