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After high school, Allen moved to Conway, Arkansas, to attend the University of Central Arkansas, where he was a business major and a member of Chi Alpha campus ministries.
but instead was persuaded to audition for American Idol along with his brother Daniel and his friend Cale Mills.
Numerous sources, including the Associated Press, claimed that the margin "wasn't even close".
He worked as a shoe salesman at a sporting goods store during the day to make ends meet and continued playing gigs in Little Rock and Fayetteville at night.
In the early stages of the season, he was among the finalists (along with Allison Iraheta) that received the least amount of screen time.
He played several instruments during his performances, including the acoustic guitar, the electric guitar, the keyboard, and the piano.
His performance of "To Make You Feel My Love" as part of the Top 11 earned praise from the judges, with Simon Cowell commenting, "I am genuinely beginning to think you have a shot of doing well in this competition." In the finals, he performed his own arrangement of "Ain't No Sunshine" on a keyboard, with a few musicians on stage, which earned praise from the judges.
This earned praise from all four judges, with Abdul remarking "There aren't many men who are willing to shop in the women's department.
You shopped and found a perfect fit." For his second Top 3 performance, Allen impressed the judges with an acoustic arrangement of Kanye West's "Heartless", prompting Jackson to state that he preferred it to West's original and The Fray's cover version.
After winning Idol, Allen made his Billboard Hot 100 debut with five songs charting within the top 100.
His coronation single "No Boundaries" debuted at number 11, followed by "Heartless" at number 16, "Ain't No Sunshine" at number 37, "Apologize" at number 66, and "Falling Slowly" at number 94.
During the final results show, he performed a duet with Keith Urban, singing Urban's single "Kiss a Girl", as well as a series of medleys with his fellow Season 8 contestants.