In The Village Voice's annual Pazz & Jop critics' poll for the year's best albums, "After Awhile" placed at number 13.[9]
The Chicago Tribune's music critic Greg Kot hailed it as one of the year's best albums[1] and wrote in Trouser Press that "it wasn’t until "After Awhile" that Gilmore's unique style became fully apparent. For the first time, the breadth of his writing is on display...For all the high-minded aspirations in the music, Gilmore never turns into a cosmic cowboy; not for nothing is he fond of quoting Ezra Pound's maxim that 'The poem fails when it strays too far from the song and the song fails when it strays too far from the dance.' The music on "After Awhile" embodies that synergy between heart, intellect and groove."[10]
The New Rolling Stone Album Guide praised "After Awhile" for "vaulting [Gilmore] into the ranks of some of the Lone Star state's finest troubadours" while observing that the album "finds Gilmore liberated from the strictures of a dancehall stage, free to serve song over form in the spirit of a folk artist rather than an entertainer."[6]
Mark Deming from AllMusic gave the record a 4.5-star rating, calling it "a subtle, unforced masterpiece that captures Gilmore at the subtle peak of his abilities."[3]
