Upon its release, "Fear of Flying" received mixed reviews from music critics citing some of the album's "tepid material." Commercially well received, the album debuted at number 15 on the "Billboard" 200 with 72,000 copies sold in its first week, and has been certified platinum by the Recording Industry Association of America (RIAA) and gold by both the Australian Recording Industry Association (ARIA) and the Canadian Recording Industry Association (CRIA). The album's lead single, "The Best of Me" (featuring Jadakiss), peaked at number 50 on the "Billboard" Hot 100. The second single, "Case of the Ex", reached number two on the "Billboard" Hot 100, while charting within the Top 20 in multiple countries. The album's third and final single, "Free", reached number 42 on "Billboard" Hot 100 and saw moderate success internationally, peaking within the top 40 in a few countries. Nearly seven months after its original release, "Fear of Flying" was re-released with two new additional songs on November 7, 2000.