Arts & Culture Archives - Mountain Brook Magazine

From Chaos, Form

Sep 3, 2025

Virginia Nelson shares her artistic passion and creative process with the community.

Full Circle

Jun 20, 2025

Tommy Mayfield finds his way back to music. By Lauren H. Dowdle | Photos by MaryMargaret Chambliss & Blair Ramsey

Student, lawyer, tech founder, consultant, mentor: Mountain Brook native Tommy Mayfield has worn many hats through the years. However, the one he keeps coming back to is musician.

In high school, Tommy and his younger brother Matthew formed a band called Inward Expedition. The pair recorded two albums while in school and performed across the Birmingham area. Their first gig was at Otey’s Tavern in Crestline Village, and they also played at events such as City Stages in Birmingham and Mountain Brook High School’s annual Battle of the Bands.

When Tommy was a senior in high school, their band won VH1’s Best Unsigned Band contest for the Southeast region. The prize for winning was playing at Memphis in May, an annual, month-long festival in Memphis.

“It was a really cool experience,” Tommy says. “The only band that played after us was Widespread Panic.”

But after graduating, Tommy says he thought his musical days were over. While his brother went on to pursue a career in music—and has since released several albums—Tommy majored in English at Vanderbilt University.

He later moved to Washington D.C. to work for International Justice Mission, which is an international human rights group. The organization has teams of lawyers and social workers who help rescue people from various forms of oppression.

“I was blown away by the needs they were addressing and that there was an organization that did that,” Tommy says.

The experience helped cultivate a passion in him to attend law school, he says. After graduating, Tommy moved back to Birmingham and practiced law at Maynard Cooper & Gale for about seven years, where he focused on business and commercial litigation.

Then in 2016, he left the firm to create a tech startup company with his wife called Wyndy, an app that connects parents with vetted college babysitters. He ran the company for about five years before hiring a new CEO and began looking for a new venture.

“I had a season where I was trying to find my next calling,” Tommy recalls. “That season lasted longer than I originally wanted it to, but that actually gave me time to spend on my music.”

He picked up the guitar, began tinkering around on the piano and got to a place where he was able to start writing his own songs. Tommy also started going with Matthew to their parents’ house on Smith Lake for a day or two to work on lyrics and melodies. While he says he’s enjoyed working with his brother again and getting back into music, it’s not something he would have predicted.

“When I graduated from high school, I thought, ‘That was fun, but that’s sort of the end of music for me,’” Tommy recalls. “It appears that after 20-some years, music was not yet done with me.”

Tommy created the band Crestwood Drives, naming it after the street he grew up on in Mountain Brook, and released the album “Everything Falls Apart According to Plan,” last September. The record features songs including “Better Days,” “Hard Roads” and “Good Woman” and can be found on music streaming services such as Apple Music, YouTube Music and Spotify.

His brother produced the album, which they recorded at Mason Music, and Tommy says Matthew did an amazing job managing all of the musicians involved.

“It was really cool to watch him operate in that capacity and see the talent he has. He brings a lot to the table given his skills and experience,” Tommy says. “My brother has been a big encouragement to me, especially early on.”

Joel Blount engineered the record, and Tommy was also joined by musicians Thomas Warren, Kyle Carpenter, Haleigh Black and Will Mason on the album.

Describing his musical style as Americana, Tommy says he’s a fan of artists including Jason Isbell, Tyler Childers, Brandi Carlile, Sanders Bohlke and Phoebe Bridgers.

“I enjoy having a variety of musical influences to draw from,” he says.

Not only have other musicians influenced his artistic style, but also writers and theologians such as T.S. Eliot, Flannery O’Connor and Robert Capon have also had an impact on him.

Yet, music isn’t his only passion. Since leaving his role at Wyndy, Tommy works with other entrepreneurs to help them on the practical aspects of starting a business.

He’s also started a new role at The Center, which provides coaching and mentoring for men. That’s allowed Tommy to share his personal experiences, like how he’s been sober for four years, with the men he meets to help them overcome their struggles.

In a way, that’s not so different from what he does with his music. The lyrics and meanings behind each of his songs are pulled from his life and experiences. One phrase that Tommy says has resonated with him is being “stewards of our scars.”

“Songs are born of certain scars I have,” he says. “But I also have a sense of stewardship because I feel like the songs were given to me to share in case they can be of service to others. Maybe the songs tap into their emotions or enable them to say something they haven’t been able to say.”

He says his family—including his wife, Ginger, and their two daughters—have been supportive throughout this journey. Looking ahead, Tommy says he plans to continue creating music and hopes to work on a new album this summer.

“I want to continue writing songs and recording,” Tommy says. “I hope to find more opportunities to perform live in the future.”

[sidebar] Supporting the Arts
Not only does Tommy Mayfield enjoy sharing his music with audiences, but he also wants to give back to local organizations that support the arts. Tommy held his album release show for “Everything Falls Apart According to Plan” at Woodlawn Theatre in Birmingham on Jan. 11, and all of the proceeds benefited the theatre.

As part of the Mason Music Foundation, the Woodlawn Theatre pays teachers to teach lessons to students there for free. Tommy says he wanted to support those efforts and everything the theatre does for artists. The 250-capacity space is owned by Will Mason of Mason Music, and Will was also one of the musicians who performed with Tommy for the show.

“I’m a huge fan of Will as a person and of his vision for the theater,” Tommy says. “The music scene and artists need spaces like that.”