I’m on the Outside Looking In was a Billboard Top 20 Pop hit, peaking at number 15. Written by Teddy Randazzo and Bobby Weinstein, this was the group’s comeback single, ending a long period of inactivity.
After the group’s first hit-making period, with such hits as “Tears on My Pillow“, “Little Anthony” Gourdine left the group for a solo career. Both he and the group released records separately, but none of them were hits.
By 1963, both entities had faded from the charts. In the interim, The Imperials had gone through some membership changes as well. While original members Ernest Wright and group founder Clarence Collins had remained with the group, the other original members, Tracy Lord and Nathanial Rogers, left the group, and Sammy Strain joined the group.
In late 1963, writer and producer Teddy Randazzo, a childhood friend of some of the group members and now a songwriter for Don Costa Productions, contacted the group, saying that he had written a song that he wanted them to record, and from that point on, things began to change for The Imperials. Gourdine, Wright, Collins, and Strain went to the studio and recorded “I’m On The Outside (Looking In)”.
With the help of New York disk jockey Murray the K, the song became an immediate hit and re-established The Imperials as a hitmaking force. This song was the first of a long string of hits by Randazzo for the group, which helped them transcend their status as a teen doo-wop group and established them as successful in the adult contemporary radio format. Wiki