For two weeks in August 1977, Mac McAnally occupied a spot on the lower reaches of Billboard pop Top Forty with an insightful bit of Life 101 called “It’s a Crazy World.” Written when he was just 16, he was 19 when the song hit. As a country songwriter, he has penned hits for Alabama (“Old Flame”), Sawyer Brown (“Thank God for You”), Ricky Van Shelton (“Crime of Passion”) and Steve Wariner (“Precious Thing”), among many others. McAnally’s biggest country hit as an artist, “Back Where I Come From,” would be cut twice by Kenny Chesney, including as a live track on his 2000 Greatest Hits LP. In addition to his songwriting, which earned him election into the Nashville Songwriters Hall of Fame in 2007, McAnally has been active as a producer and backing musician for decades. He holds the record for the most CMA Musician of the Year trophies, collecting eight in a row from 2008 to 2015, with another nomination this year. A longtime member of Jimmy Buffett’s mighty Coral Reefer Band, a gig McAnally holds to this day, the latest project the humble, self-effacing Mississippian is involved in is one reaping rewards of an entirely different sort.

His just-released LP Southbound is McAnally’s first-ever exploration of the songs in his extensive catalog, couched in an orchestral setting. An adventurous album brimming with heart, soul and wit, it was conducted by University of Southern Mississippi Music Director Jay Dean and features student musicians from the Hattiesburg-based school’s symphony orchestra as well as McAnally’s fellow members of the Coral Reefer Band. While the album beautifully illustrates Mississippi’s rich cultural heritage, McAnally is also using its release to help his home state, which has the largest number of documented food-insecure individuals in the country. Proceeds from the LP are being split between the University of Southern Mississippi’s music program and Extra Table, the charitable organization founded by acclaimed Hattiesburg restaurateur Robert St. John.

Did you feel pretty confident early on that the concept of an orchestral record of your songs would actually work this well? Or did you have some doubts?

Well, there’s no aspect of me as a recording artist that is not pretty well-doubted! [Laughs] I’m a bashful guy, and I’m not the most self-confident by nature, but this batch of songs, particularly maybe in four or five cases, these were songs that all my life I’ve really wanted another shot at singing. Partially because I’m such a bashful guy, I’ve never been the most confident singer. I’m more of a background singer.

How did you land on the idea of supporting Extra Table in particular?

It’s a Mississippi-centric charity, and that’s where I come from. I have a few songs talking about how proud I am to be from there. And they’re on this record, for the most part. I am very proud to be from Mississippi, but the reality is that my home state is either number 50 or number one in most things. We are one of the poorest states and because of that, according to the statistics, there are about six to 800,000 under-nourished… “food-insecure” is the term that they’re using these days.

The record also benefits the university’s music program. Why was that important for you?

Jay Dean has, for 30 years, been bringing not only the best players that he can find in Mississippi, but he’s been bringing players up from South America that came out of really abject poverty, that are really gifted musicians. He’s been sort of a pipeline for Brazilian and Chilean, quite a few South American musicians, over 300 now. So this orchestra that played on this is made up of students, and some faculty that are those people who have been through his program.

You also have some of your Coral Reefer Band comrades on the album. Where did you do the recording?

We went down to Mississippi and recorded the orchestra down there and we recorded at my studio down in Muscle Shoals. The Coral Reefer Band is like a second family to me, so everything about this felt good. Mr. Buffett is an alumnus of Southern Miss, and that helped him loan me the rest of the Coral Reefer Band. All the good will that went into every aspect of this, I believe that shines through. Even in the [LP] cover work. I was talking to the girls that did the cover about wearing old feed-sack shirts that were made out of flour sacks and, in some cases, out of old fertilizer sacks. Out of the Depression, that’s what folks made their clothes out of. And they took that conversation and made the cover look sort of like an old feed-sack. I realize that’s a minute detail, but just the fact that everybody involved in this got that involved in it, to me, makes it that much richer of an experience.

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