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Fictional musician Dewey Cox begins his quest for greatness from humble beginnings in Springberry, Alabama. While playing with his brother Nate in a sequence of needlessly careless and dangerous acts, he accidentally cuts his brother in half at the waist (a reference to Johnny Cash's older brother Jack, who was almost cut in half by a table saw and died from his injuries). This leads Dewey's father to frequently repeat the phrase "The wrong kid died." It is this traumatic event that motivates Dewey to rise to stardom and "be double great for the both of them." (which is also a reference to Elvis Presley, whose twin brother was stillborn), while at the same time making him lose his sense of smell. After his brother's death is announced by a physician making a housecall, his mother sends him to the local store to buy a candle. There, he meets a black blues guitarist, who lets Dewey play his guitar. Dewey is a natural. The scene was likely a reference to country icon Hank Williams, who was introduced to the guitar by a black blues guitarist Rufus Payne.

After a successful, yet controversial, talent show performance that is reminiscent of an early, sugary Buddy Holly rock song, a then 14 year old Dewey decides to leave Springberry with his 12 year-old girlfriend Edith (Kristen Wiig) They soon marry and Edith begins to criticize Dewey and insist that his dream of being a musician will never happen. Inspired, Dewey then delivers the "Walk Hard" speech, which is the origin of the lyrics of his number one hit record. While working at a nightclub, Dewey gets a break when he replaces singer Bobby Shad (Craig Robinson) at the last minute, much to the delight of the Hasidic Jewish executives at the show. Dewey then is brought to the studio where he first records "Walk Hard."

Within 35 minutes, the song becomes a hit, and Dewey begins to get caught up in the fame of rock and roll. He starts to hang out with musicians such as Elvis Presley and later, The Beatles. With the addition of backing singer Darlene Madison, (Jenna Fischer) Dewey produces more hit records. Around this time, drummer Sam (Tim Meadows) introduces Dewey to marijuana, which causes him to become unfaithful to his first wife Edith in more ways than one. Pa then returns to inform Dewey that Dewey's mother has passed away. Pa manages to make Dewey feel responsible for her death, contributing to an already high level of inner turmoil. He then gets married to Darlene while still married to Edith, which leads to both of them leaving him. Dewey eventually is busted after purchasing cocaine from an undercover cop and serves time in jail before Darlene returns.

They then move to Berkeley, California in 1966 at the beginning of the '60s counterculture movement. During a visit with The Beatles in India, Dewey and Darlene take LSD, which causes Dewey to lose touch with reality yet again. Dewey becomes obsessed with every aspect of the recording process and is completely consumed with creating his masterpiece. In a reference to the landmark album Pet Sounds, a live goat is literally bleating on the track. Darlene is unable to deal with Dewey's insanity and leaves him again. After another stay in jail and rehab, Dewey is next seen jogging into the 1970s. Now working on a variety television show (which could be a reference to Elvis' Las Vegas era), Dewey continues to try to write a masterpiece for his brother. However, Dewey comes to realize what is most important and begins to focus on spending time with his numerous children.

Darlene then returns once again, this time in 1992 as Dewey begins his senior years. Then, in 2007, Dewey becomes popular with younger listeners through rapper Lil' Nutzzak's remix of "Walk Hard," Dewey is awarded a lifetime achievement award. He is finally able to fulfill his wish of creating one great masterpiece with his final song "Beautiful Ride." He dies three minutes after the performance.