A persuasive case could be made that Don McLean’s “American Pie” is the most iconic song ever written, though officially speaking, it’s the fifth top track of the 20th Century according to the Recording Industry of America (behind only Judy Garland’s “Over The Rainbow,” Bing Crosby’s “White Christmas,” Woody Guthrie’s “This Land Is Your Land” and Aretha Franklin’s “Respect”).

Besides helping land the Grammy-winning troubadour in the Songwriters Hall of Fame and fetching a whopping $1.2 million winning bid for a handwritten lyric manuscript with full explanation (that he’s always avoided during interviews), it’s been regularly remade by the likes of Madonna, Garth Brooks and now Home Free.

To mark the chart-topper’s 50th anniversary, McLean promises a tour just as soon as its possible, though in the meantime, there’s the new studio album “Still Playin’ Favorites,” which is comprised of soulful and southern covers originally cut by Mahalia Jackson, Johnny Cash, Ray Charles, Bob Dylan, Bessie Smith and many more.

Chicago Concert Reviews was grateful to speak with the man who so eloquently personified “the day the music died,” in addition to the Elvis Presley standard “And I Love You So” (also Prince Harry and Megan Markle’s wedding theme), the 2Pac-praised “Vincent (Starry, Starry Night)” and a couple Drake-sampled “Prime Time” tunes, to name but a few of the many penned by the treasured troubadour.

What came to mind when you realized this is the 50th anniversary of “American Pie”?

Don McLean: I think it’s a very elegant year, 50 years of something, sort of stately and grand. It’s not like, “oh, it’s been out six months.” It certainly lasted all these years, so that anniversary carries with it a certain gravitas, I guess you might say. It makes me proud that, for whatever reasons, the song has remained important to a lot of people. Nobody likes everything, but there comes a point when a piece of art or music becomes accepted as part of America and that’s where this is now.

It’s of course been covered by countless artists. What’s your opinion on a few famous ones?

McLean: Anytime I get a nice cover version of a song of mine, I get down on my knees and thank the Lord cause it’s a wonderful thing to have other artists appreciate your music and do it, younger ones like John Mayer and Bon Jovi, who’s not that much younger, but they’re also doing it. This group called Home Free has an a cappella version out now, which is number one on all the country video charts. The song has still got a presence and a place for it in the world. It’s pretty thrilling really. It’s like I’ve never grown old. I’m always young.

You actually joined Home Free on their version. What was your vision for that?

McLean: There was no vision on my part. It was all their doing. They did the video, they put the whole thing together, they did the soundtrack and all I did was the front, the end, some other things they asked me to do and then appear in the video. No, they were entirely in charge of that and that’s the way I like it. Tell me what to do. I love it.

Just prior to that in late 2020, “Still Playin’ Favorites” became your sequel 1973’s “Playin’ Favorites.” Was that long of a gap intended or did it just wind up that way?

McLean: I don’t live near a studio, so I don’t go into studios that much. [The last time] I went in, I laid down maybe 50 tracks. I had a lot of new songs for the [2018] album “Botanical Gardens.” Then I had like another 20 tracks and I created the “Still Playin’ Favorites” album with a lot of fun songs that I do with the band. I’ve still got another ten tracks laying around I haven’t used…I could’ve done ten different albums and called it “Still Playin’ Favorites,” easily.

How did you go about choosing the tunes you wanted to remake?

McLean: You know, just whatever comes to mind when I’m with the band in the studio. Of course, I had the agenda for the album, “Botanical Gardens,” and that was strict. I knew what I was wanting to do and that was primary, but then I’d take a break and we’d play something like [Webb Pierce and Mel Tillis’] “I Ain’t Never” or some fun song that we would do on the road, just do it two or three times and get it in the can while everybody was happy. The way we make records is the way they used to make records with everybody together, having a good time and the energy of doing what hits you at the moment.

Going back to another one of your regularly redone songs, “And I Love You So” was a hit by everyone from Elvis Presley on down. What has that attention meant to you?

McLean: That has a whole history to it. I put it out and it immediately got into the top 100, which was a surprise for me. That’s not a big accomplishment, but for me it was because I had never imagined I’d ever see a song of mine on the charts. That was a big shot in the arm and then everybody else started to record this song, selling a lot of records with Johnny Mathis, Andy Williams and there were a lot of pop singers around in those days, men and women, that all did my song. It was like a Vegas favorite and then it became a country favorite. I happen to know Willie Nelson and Emmylou Harris have done it, so it just crosses the board. Then in ‘75, Perry Como does it, has a million seller and its number one worldwide! So I think “wow, this is like the end. It can’t get any better than this!”

The next year, Elvis does it. He did it every night for the last two years of his very sad life. It ended up being the last song on the last side of “Elvis In Concert,” which is the last album that he ever released in his lifetime. Now I just got a triple platinum award from RCA for that song being on that record. It’s on my wall with so many others. I have so much gold and platinum up here, it would knock your socks off. It’s pretty amazing.

What’s an unexpected one that wound up on the wall?

McLean: Drake’s version of “Doing It Wrong” is probably the most unusual. That’s a quadruple platinum song that I own 60 percent of because Drake used two of my songs to write the lyrics to his song. It’s from an album called “Prime Time,” which is an underrated album and a very important record, in my opinion, of the things that I do. I like it a lot and he liked it a lot, so he found these two songs, “The Wrong Thing To Do” and “When A Good Thing Goes Bad,” and sits down to write “Doing It Wrong.” It sold four million records and we are partners on that one!

Fellow rapper 2Pac was a fan as well, especially of “Vincent.” Your thoughts?

McLean: His mother is a lady named Afeni Shakur and she was a Black Panther. When 2Pac died, a few years after they did a documentary about him and Afeni said, “you must include Don McLean in this documentary,” so I am in the documentary, very prominently featured. The songs that I wrote meant a lot to him and it just deepens my belief in people and my love of America. You just don’t know what people are thinking, what moves them and what touches them. We are all so quick to make stereotypes at people. Here’s a rapper who got shot and killed, and his favorite song was “Vincent,” so what are you gonna do about that? That should make people realize something, that the road he takes has to do with the options he has.

What other tracks would you like to be revisited or remembered like these classics?

McLean: Oh, well, there’s a lot. I think a lot of my songs are underrated and they will be discovered by younger artists, songs like “Orphans Of Wealth,” which is about poverty in America, and “Tapestry,” which is about the environment. [Another would be] “Headroom” and the song “Prime Time,” which is about America as a game show. Everything I’ve ever done is going to be discovered and utilized. I will be looked over. Every interview will be listened to, every word, everything, will be catalogued when I’m gone, believe me.

I’m sure you’ve met every artist imaginable, both young and old, along the way. Who are some of your closest relationships?

McLean: I haven’t met that many artists, to tell you the truth. I’ve seen as many as I could on stage and worked with a number of them, but I’m really not a guy who networks with anybody. One of my favorite people that I ever knew was Chet Atkins, who was basically the architect of modern country music and a great producer. I used to see him a lot when I would go to Nashville.

What about current country superstar Garth Brooks?

McLean: Garth is a fellow who I’ve met and worked with a few times. He is a national treasure, a fantastic person and a very strong person. He controls the environment around him in a very good way. I admire him and I like him a lot.

Another A-lister that’s had huge success with your music is Madonna.

McLean: Madonna is in a class by herself. I mean, there’s no one like Madonna at all. She is the closest thing we have to Elvis Presley, I think now, in terms of her cultural impact, but fortunately, she takes good care of herself. She’s always busy and never stops with the hits. I mean, she’s always scoring with something and I’m sure we’ll hear about her soon. She’s had a lot of criticism in her life and still keeps doing what she needs to do, so I really admire that. That’s hard.

Early on, you also faced the challenge of being rejected 72 times by record labels, if the internet is accurate. Any wisdom for a newcomer wanting to follow your path?

McLean: No, it’s about 30 times. That number’s high…I didn’t have anything else that I was any good at, so all I could do was bang away at trying to make a record, write my songs and build an audience. That was the only option that I had. I wasn’t a great student or a great athlete. I didn’t have any money in our family and my father had died when I was 15, so basically I was on my own from that time. I had my mother and my mother was a very important influence on me, but I knew what I was gonna do and I knew what I was good at. I suppose if I had well to do parents and my father was offering me a job to come work with him that I would’ve been weak and I never would’ve done what I did. I would’ve said “okay, Dad, I’ll work with you.” A lot of people get roped into something like that cause they don’t want to disappoint their parents or they don’t want to really struggle for some dream that seems a little bit far-fetched, but in my case, it wasn’t far-fetched because it was all I had. It was everything to me and I was working at getting people to believe in me. The key is finding somebody who knows how to navigate the uncharted waters of the music business and show business who believes in you. It’s hard to find, but I had a good judge of that. I could tell when somebody was really impressed with me and was gonna really work hard for me.

Can you recall any of your earlier shows in Chicago? And what about recently?

McLean: I remember a bunch of things. First of all, when I was at my height, I played McCormick Place. I think it was a pretty big deal. I remember [when I was] flying out, I got a telegram from Hugh Hefner to come to the [Playboy] mansion. I was on the plane out of town when I read it, but I wouldn’t have come anyway. It was kind of funny and I saved it. Then I remember some of the places in Chicago before the things really got going, like the Ivanhoe [Castle Theater & Restaurant], I think. Another good place is Park West and doing some nice festivals in the summertime. It’s a good music town, it really is.

What’s coming when you return to the road?

McLean: They’ll be brand new songs from this album that hasn’t been released yet and from the last record, “Botanical Gardens.” Then I’ll dip into my song bag and I’ll do pretty much all the songs that people love to hear: “Vincent,” “American Pie,” “Castles In The Air,” “And I Love You So,” “Crossroads,” “Winterwood,” that kind of stuff. I don’t do the same set every night.

Anything to add during this unusual season of waiting and wondering?

McLean: Well, you don’t have to worry about Don McLean. I’m in heaven. I’m doing all the things I want to do. I’m in good shape to go back to work on the road if that comes along the way I want it to. I have done a lot of things that I wanted to do in this pandemic year. In order to be happy, you have to have a flexible mind. Rather than looking back over the year and thinking about what you lost, that is unless you’ve lost ones to this illness, which is a whole different thing, [when it comes to] money, time or opportunity, be flexible mentally. This year, I’ve done all this stuff I’ve been doing, but I also learned how to cook. I really enjoy it, so I opened up a whole new area that I didn’t have the time to do before!

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For additional information on Don McLean, visit DonMcLean.com.