Ironically, Harry is where Harry Nilsson began to become Nilsson, an immensely gifted singer/songwriter/musician with a warped sense of humor that tended to slightly overwhelm his skills, at least to those who aren't quite operating on the same level.
This aspect of his personality surfaces partially because the record is a crazy quilt of originals, covers, bizarre Americana, quiet ballads, show tunes, and soft-shoe shuffles.
It doesn't really hold together, per se, due to its lack of focus (which, if you're a cultist, is naturally the reason why it's charming).
Due to the sheer number of shuffling nostalgia trips, it seems as if Nilsson is attempting to sell the entire album on personality and, to anyone who isn't converted to his unique perspective, these may the moments that make Harry a little difficult to take, even with songs as expertly constructed as the delightful "Nobody Cares About the Railroads Anymore," an attempt to ape Randy Newman's Tin Pan Alley style.
Then, there are the songs that really work, such as the sardonically cute "The Puppy Song," the gentle "Mournin' Glory Story," and "I Guess the Lord Must Be in New York City," a thoroughly winning folk-rock song he wrote for Midnight Cowboy but which was rejected in favor of "Everybody's Talkin'." These are the moments that deliver on the promise of his first two records, while the rest suggests where he would go next, whether in the immediate future (a cover of Newman's "Simon Smith and the Amazing Dancing Bear") or several years later (the weird in-jokes and insularity of portions of the album, which would become his modus operandi as of Nilsson Schmilsson).