And the winner is: original releases.
This one at first appears to be close from the waveforms. The
Outside Looking In tracks are not brickwalled, though they are slightly louder than the originals (confirmed by calculating the average RMS and comparing). A listening comparison, however, reveals the tracks on the newer disc to be a bit compressed relative to the originals. This is evident from the very first song, "Follow You Down," where the compilation disc is lacking some of the higher end by comparison with the version found on
Congratulations I'm Sorry. Worst of all is the version of "Til I Hear It From You" found on the hits disc, which is very obviously compressed relative to that found on the "Follow You Down" single. In all honesty, there's really not much need to purchase the "hits" CD to begin with, as original copies of the first two major label albums are extremely common and inexpensive to obtain. I've seen used copies of
New Miserable Experience in particular countless times in bargain bins for prices as low as $1 per copy. And fully half of the selections featured on
Outside Looking In are found on that album alone. "Til I Hear It from You" is available on many editions of
Congratulations I'm Sorry, and also on the
Empire Records soundtrack album and the "Follow You Down" single. Although two songs - "Alison Road" and "Mrs. Rita" - are listed in the CD liner notes as originating from the
Up and Crumbling EP, the versions on
Experience are the same recordings (just with a better, warmer mastering job), leaving "Just South of Nowhere" as the only song on the "best of" album that you would need the EP for. The one song that's nearly exclusive to the compilation disc is a live version of "Whitewash" (previously available only on one particular version of the "As Long As It Matters" maxi-single), which may or may not be important enough to justify paying for a collection of otherwise pretty easily available material. I tend to view live recordings that weren't singles as filler when included on these kinds of compilations, particularly when included in lieu of the original studio recordings, and so for me it's not worth shelling out full album price for this one song. Your mileage may vary, though.
As a side note, the spelling of "Allison Road" is inconsistent between releases, with both Up and Crumbling and New Miserable Experience listing it as "Allison Road" with two Ls, while the Outside Looking In release uses only one ("Alison Road"). In addition, the stereo of the New Miserable Experience songs is reversed on the later compilation disc.