Walk into Phil Proctor’s classroom at McGill-Toolen Catholic High School and the first thing you notice is the wall. It is covered, edge to edge, with carefully arranged posters: rock bands like R.E.M. and Wilco hang beside blues giants such as Muddy Waters and Little Milton. For the teenagers who take his Southern culture elective, the display is a strong hint about their teacher’s other life. For much of Mobile, Phil Proctor is best known as a musician, one of the most in-demand guitar, mandolin and vocal talents on the local live scene. At McGill-Toolen, he is simply Mr. Proctor, a history and social studies teacher who has helped shape several generations of students.
The two roles, it turns out, are closely connected. The images on his wall are not just decoration, and the curiosity that drives his teaching is the same curiosity that sends him down back roads on the way to gigs. This profile, first shared in October 2025, looks at how one Mobile educator has balanced a demanding teaching career with a performing schedule that would exhaust most full-time musicians.
A Classroom Wall That Teaches
Proctor says the posters were chosen to support the material he covers in class. Not all of them are about music.
“Some of them are music related, but others are from arts and literature, or maybe they’re historical or relate to the natural history of the South,” Phil says of the images on the wall. “They are mostly things that relate to what we cover in the Southern culture class, and most of them are things that I like, too.”
That mix reflects the breadth of the subject. A course on Southern culture can touch everything from agriculture and economics to literature, religion, food, folk art and the region’s landscapes. Music is an obvious thread. The American South gave the world the blues, country, gospel, jazz, rhythm and blues, and early rock and roll, and bands such as R.E.M., which came out of Athens, Georgia, carried Southern influences into alternative rock. Muddy Waters, born in Mississippi, helped carry Delta blues north to Chicago, where it was electrified and went on to influence generations of rock musicians. Little Milton, another Mississippi native, became a major figure in blues and soul. Putting those figures on the same wall is a visual way of showing students how deeply the region’s culture runs through American life.
From Huntsville to Montevallo to Mobile
Proctor is a Huntsville native. He studied art and history at the University of Montevallo, the public liberal arts university in Shelby County known for its strong programs in the arts. While there, he played in rock bands, and he also met his future wife, Shelly, a Mobile native. That connection eventually brought him to the Port City.
His first years in the Mobile area were spent in retail, working at Peaches Records & Tapes, part of a once-popular regional chain of record stores. Then he heard that McGill-Toolen needed substitute teachers.
By then, Proctor had long been drawn to the visual arts, including photography, and history had become a growing passion. He traces that interest to a very personal project.
“It really started blossoming when I was doing my own genealogy,” he says. “Then, I could draw some parallels, like what my grandfather was doing during the Spanish-American War. That made history a lot more interesting to me because I had a personal connection.”
The habit stuck. He began leaving early for band gigs so he could take the back roads and catch glimpses of how things used to be. It is something he still tends to do when time allows, turning the drive to a show into an informal field trip through the region’s past.
Building a Teaching Career at McGill-Toolen
After only a few months of substitute teaching, McGill-Toolen hired Proctor full time. He then took advantage of an incentive program in which the school paid half of his tuition while he attended night classes at Spring Hill College, earning his master’s degree. During the same stretch, he was also teaching guitar lessons part time at West Mobile Music. The combination of full-time teaching, graduate school and private lessons says a good deal about his work ethic.
Both institutions in that part of his story carry deep roots in Mobile. McGill-Toolen traces its history to the McGill Institute, a Catholic boys’ school that opened in the late 1800s, and it took its current name after merging with Bishop Toolen High School, a Catholic girls’ school, in the early 1970s. Today it is one of the largest Catholic high schools in the Southeast and is operated under the Archdiocese of Mobile, with a campus in Midtown Mobile. Spring Hill College, founded in 1830, is the oldest Catholic college in the Southeast and a Jesuit institution whose campus is known for its avenue of live oaks.
More Than 200 Gigs a Year, While Teaching
Anyone who follows live music around Mobile Bay knows Proctor’s name. For a time, he was playing more than 200 performances a year, all while holding down a full-time teaching job.
“It’s a lot less than it was, but it’s still well over a hundred gigs a year,” Phil says. “I’d say that in the year or two leading up to COVID, I was playing 220 gigs a year. It was crazy. Now I probably average 10 to 12 a month.”
Even the reduced pace is impressive. When this profile was written, Proctor was playing once a week at Callaghan’s with the popular duo Phil & Foster, in addition to frequent solo performances. He has played in a number of other configurations, including the Marlow Boys, and he is known as a nimble and dependable fill-in with Rollin’ in the Hay. Over the years he has also performed around the area with acts including:
- Phil & Walon
- Daddy Longlegs
- The Dog River Boys
- The Deluxe Trio
- Suburban Jazz Quartet
- The Mobile Big Band Society
The range of that list, from bluegrass and roots music to jazz and big band, helps explain why other musicians respect him. Callaghan’s Irish Social Club, the Oakleigh Garden District neighborhood bar where he has held a regular slot, is one of Mobile’s best-loved small music rooms, a place where audiences sit close to the players and good musicianship is noticed.
Proctor says the shutdowns during the COVID-19 pandemic led him to rethink how much he was playing. With live music on pause, he realized he enjoyed having more time for other pursuits, especially time with Shelly and their three children: twin sons Jack and Sam, and their younger sister, Maggie. When music returned, he became more selective about which gigs he accepted, instead of taking most of what came his way.
Offers keep coming for a simple reason: he is very good. Proctor is a multiple repeat winner of Best Guitar Player in Mobile’s annual Nappie Awards readers’ poll, and he has also been recognized in the same poll as Coolest High School Teacher. He is quick to wave off the honors as something of a popularity contest, but fellow musicians regard the recognition as well earned. They admire his skill across a wide range of styles, a versatility that is rarer than it might seem.
Bridging the Generation Gap
Proctor hopes to give his students the same spark he felt when he first traced his own family history. In his elective on Southern culture, he recently asked a room of juniors and seniors to come up with marketing ideas for farm commodities. The assignment was part of a unit on agriculture meant to help students understand how the South became what it is today, a region whose economy, settlement patterns and social history were shaped for centuries by crops such as cotton, tobacco, rice, sugar cane and timber.
To get them started, he used the once-ubiquitous “Got Milk?” advertising campaign as an example. Few, if any, of the students recognized it. The campaign, launched in the early 1990s, was a pop culture fixture for years, but it predates everyone in the room.
That moment illustrates a challenge every longtime teacher faces as the age gap widens. Proctor has a good-humored way of describing it.
“I like to describe it as a Venn diagram,” Phil says. “When I started teaching, my circle and the students’ circle overlapped a good bit, and now they just barely touch every now and then. I just try to stop making cultural references and then being amazed that they don’t know who the Beatles are or something like that. I get it and I’m over that. They may not know how to tell time with an analog clock, but I don’t beat them over the head about it because we hardly use them anymore, anyway.”
He pauses, then adds: “I never learned how to hitch up a team of mules, either, so I don’t think I can fault them for not knowing how to read an analog clock.”
It is a historian’s answer. Every generation’s everyday knowledge becomes the next generation’s history lesson, and Proctor’s approach is to meet students where they are rather than lament what they have missed.
The One Day the Guitar Comes to School
Proctor usually leaves his instruments at home. But the Southern culture course includes a unit on the blues and its role as a cornerstone of modern American music, and that unit gives him a legitimate reason to bring a guitar to class.
The blues are an ideal subject for a Southern culture course. The form grew out of African American communities in the Deep South in the late 1800s and early 1900s, drawing on work songs, field hollers, spirituals and ballads. From the Mississippi Delta and other parts of the region, blues musicians carried the music north during the Great Migration to cities such as Chicago, Detroit and St. Louis. Its twelve-bar structure, its “blue” notes and its call-and-response patterns became the foundation for rhythm and blues, rock and roll and much of the popular music that followed. Alabama has its own deep ties to that story, and the state’s contributions to blues, gospel, soul and country are celebrated at institutions such as the Alabama Music Hall of Fame in Tuscumbia.
For students who may know the music only through a streaming playlist, watching their teacher demonstrate a shuffle rhythm or a slide lick in person can turn an abstract lesson into something they are unlikely to forget. It is the rare moment when the two halves of Proctor’s working life meet in the same room.
A Model of the Working Musician-Educator
Mobile has a long tradition of musicians who also hold day jobs, and many of the area’s most respected players have been teachers, whether in classrooms, private studios or music stores. Proctor’s story fits squarely in that tradition. He has spent decades teaching teenagers about the history of the region by day, and then playing some of the music that grew out of that history at night.
For readers who want to hear him, the best approach is to watch local venue calendars and the social media pages of the groups he plays with, since schedules change often. Callaghan’s, in particular, posts its live music lineup regularly. And for McGill-Toolen students lucky enough to land a seat in his Southern culture class, the lesson is already clear from the wall: history, art and music are not separate subjects in the South. They are all part of the same story.