Diary of a Melomaniac

Comparing these two, Naughty’s Nicest (Rhino) has three songs not on Nature's Finest (Tommy Boy):

"Everyday All Day" – from debut

"Yoke the Joker" – from debut

"Dirt All by My Lonely" – from Nature's Fury

And Nature's Finest has four songs not on Naughty's Nicest:

"Penetration" – actually a Next song, feat. NBN

"Clap Yo Hands (Remix)" – from Poverty's Paradise

"Nothing to Lose (Naughty Live)" – from Nothing to Lose soundtrack

"Naughty by Nature (The Megamix)" – previously unreleased

If you discount the megamix, which one should, then they have an equal number of tracks. As far as regular-issue albums, Nature's Finest has five tracks from the debut, while Naughty's Nicest has seven. They both have the same two tracks from Poverty's Paradise, although Nature's Finest adds a subpar remix of the best track, "Craziest." They both have the same three tracks from 19NaughtyIII. Finally, Naughty's Nicest has one from Nature's Fury.

Essentially, Nature's Finest over Naughty's Nicest gets you a live track (!) and a subpar Next r&b song, so, essentially nothing, while Nature's Finest gets me the three album tracks listed above. Also, since I don't really like the debut, but it's considered "their best" by many, Naughty's Nicest gives me seven whole tracks from that. Bottom line: Naughty's Nicest is the no-brainer. Plus, it's sequenced via album, not all over the place, no megamixes, live tracks, r&b songs by other artists featuring NBN, subpar remixes of their best track, etc. No big surprise that Rhino did a better reissue job than the original label, Tommy Boy. A great label, but still, not a reissue specialist.

[TL;DR: Nicest - 13 album, 3 soundtrack | Finest - 11 album, 3 soundtrack, 1 live, 1 megamix, 1 Next]