The former Wee frontman, now a year removed from his 31-year prison term, celebrates the 40th anniversary of 'You Can Fly on My Aeroplane'

On May 2, 1971, Norman Whiteside performed at the Ohio Theatre in a talent show that served as a tryout for a new local record label, Capsoul. If he could win over label head and colorful radio DJ Bill Moss, Whiteside could walk away with a recording contract.

He didn't make the cut. But Whiteside's combination of charm, talent and determination often allowed him to hurdle whatever life put in his way. As a child, he played drums in a family band, but he wanted to play piano. His aunt had a piano, but in order to play it, Whiteside had to work at a landscaping company from 7 a.m. to 4:30 p.m., six days a week. Afterward, he was allowed to play the piano from 5:30 to 10 p.m.

And so, after long days of cutting grass and trimming hedges, Whiteside taught himself to play the piano, listening to songs by Stevie Wonder, Isaac Hayes and Al Green and trying to copy what he heard. After a full summer of yard work and piano, his mother asked him to play something for her.

“I played a song called ‘Exodus,'” Whiteside said on a recent weekday at the headquarters of the William Brady Charitable Organization on the East Side. “She said, ‘Oh, my gosh. You got to play this in church.' She wanted everybody to know that her baby could play the piano.”

At 16, Whiteside's grandfather cosigned on the purchase of a Wurlitzer piano and two Leslie speakers. Whiteside holed up in his room for hours playing piano, singing and teaching himself to play bass. He'd go on to work with Moss and others at the short-lived and long-respected Capsoul, but Whiteside never quite fit in. Capsoul was going for a classic Stax sound, but Whiteside liked to experiment with new sounds. “I was listening to people like Gino Vannelli, Todd Rundgren and Carole King,” he said.

According to Whiteside, Moss told the young musician his music was too futuristic. “I didn't know whether to take that as a compliment or what,” Whiteside said. “I did not know that his words for my music would ultimately become the truth. What he was saying was prophetic.”

Eventually, Whiteside would front the band Wee and release his 1977 magnum opus, You Can Fly on My Aeroplane, which veered sharply from the Capsoul sound, incorporating more electronic sounds, psychedelic guitar licks and Whiteside's “dark, mystic chords.” It was soul from the future.

But Whiteside's personal life, which at one point was filled with more sex, drugs and crime than a Martin Scorsese film, eventually derailed his music career. In 1982, Whiteside was convicted in the death of Denison University student Laura Carter, who was killed by a stray bullet in a gang-related shooting. Whiteside wasn't present at the shooting and maintained his innocence, but he was sentenced to 37 years in prison.

Whiteside continued to play music in prison, and his big break came when Chicago archival label Numero Group, which had already re-released some of Whiteside's Capsoul music, reissued You Can Fly on MyAeroplane in 2008. From there, the songs made their way to the likes of Kanye West, who used part of Aeroplane's title track on the song “Bound 2.” Word of his talents spread, and in 2016, the Ohio Parole Board set Whiteside free after 31 years.

These days, Whiteside spends much of his time volunteering with the William Brady organization, a nonprofit tasked with “helping people cope with mental illness through beautiful music.” Brady will play drums for Whiteside in a concert at the Phenix Banquet Center on Friday, Oct. 20, to celebrate the 40th anniversary of Aeroplane.

Whiteside promises a special night of music, but not because of any glitz, glam or window dressing at the show. “We don't have to bring out spaceships and make you look at the spaceship. We present the music. All of the cosmetics we can do without,” Whiteside said. “Did you pay to see the lights, or did you pay to see the entertainer and listen to the music?”

Forty years removed from Wee's masterpiece, Whiteside said he has nothing to prove. The anniversary show is merely a way to present songs that feel as special to him today “as when they first went through my body,” he said. “Music is a gift. I might write it, but it doesn't belong to me. Therefore, I gotta give it to everybody it belongs to. … We're trying to give people a good feeling about something that they dreamed about a long time ago. And some of the people who were babies when this came out, they're gonna say, ‘Wow.'”

Whiteside might never have made Aeroplane if he'd admitted defeat on May 2, 1971. Instead of sulking after the talent show, he found Capsoul's studio, located in the back of Van's music store in Clintonville. So, as Whiteside tells it, one day he showed up, put his ear next to the huge, black, metal doors and heard music. He banged on the doors with his fist, over and over, until someone noticed. Eventually, Capsoul musicians and songwriters Dean Francis and Jeff Smith came to the door, but they wouldn't let him in. “Young man, this is a closed session,” Smith said.

Whiteside protested, but they wouldn't relent. So he returned a few nights later and lay down in front of the door until Bill Moss himself came out to see him.

“What are you gonna do if I don't let you in?” Moss said.

“Sir, I'll just sleep right here and listen,” Whiteside answered.

“Boy, you crazy,” Moss said. “Come on in.”