Milestones, memories and moving forward are just a few of the themes that jump out on the kaleidoscope of a calendar for the 2020 installment of Ravinia Festival, America’s longest-running musical institution of its kind.

For starters, the freshly-announced line-up includes the venue debut for Jesse & Joy (Jun. 12); Musiq Soulchild opening for Jill Scott (June 14); Ruben Studdard from “American Idol” singing the Luther Vandross songbook prior to Patti LaBelle (June 18); Black Violin with Soul Children Of Chicago and Blind Boys Of Alabama (Jun. 20); Tonic joining Collective Soul and Better Than Ezra (June 24); Ani DiFranco co-headlining alongside the Indigo Girls (June 26); King Crimson and The Zappa Band (July 5); Brian McKnight and Macy Gray (July 14); Ziggy Marley celebrating the 75th birthday of his father Bob Marley (Aug. 12) and The Australian Pink Floyd Show (Sept. 2), amongst many others.

Then of course there’s the highly heralded return of Sheryl Crow (Jun. 13); Judy Collins and Arlo Guthrie (Jun. 17); Carrie Underwood (Jul. 18-19); Chick Corea & The Spanish Heart Band with Rubén Blades (Jul. 24); Willie Nelson & Family (Aug. 2); Train plus Vertical Horizon (Aug. 21-23); Bryan Ferry (Aug. 24); Diana Ross (Aug. 26); Tony Bennett (Aug. 29); Gladys Knight and Heather Headley (Aug. 30); John Legend (Sept. 6); Ms. Lauryn Hill (Sept. 11) and The Beach Boys (Sept. 12) to name but a few from an entire summer’s worth of stars.

It also marks the swansong season for Ravinia Festival President and CEO Welz Kauffman after exactly 20 years, who connected with Chicago Concert Reviews for extensive insight on booking the pop side of an immensely varied roster that also abounds with jazz, classical and cross-cultural engagement opportunities adding up to a whopping 120 events from May 30 through September 15.

There are several exciting and surprising debuts this summer. Tell me about a few that are really getting people chatting.

Welz Kauffman: Black Violin is one show that really excites me a great deal, not only because I’ve been working hard to get them for a long time, but because they represent a successful example of crossover. They’re tremendously gifted string players who do all different types of genres, but one of their motivations is to expand a listener’s ideas of what they might want to listen to, including classical music.

I’ve been wanting [King Crimson and The Zappa Band] for so long I kind of feel like they have been at Ravinia before. It’s a very natural pairing. That progressive rock piece of American music history is something that we haven’t had a chance to explore and I think this is going to be a great show for just that.

We love celebrating birthdays and anniversaries at Ravinia. All classical music institutions do, but we like doing it in all genres and it is the 75th birthday year for Bob Marley. The entire [Ziggy Marley] show will be covers of his father’s music, so people who are expecting that Marley sound and tunes will get every bit of that this summer at Ravinia.

Reuben [Studdard] has a wonderful album of all Luther Vandross songs. I was given that for a holiday gift and just loved it. When I started to work on the possibility of the legendary Patti LaBelle returning to us, it was actually her management that suggested Reuben because they’ve done some co-headlines before and they had a great time together.

Out of all the returning artists, who are some of your favorites?

Kauffman: I was talking to a DJ yesterday and it’s interesting because I asked that question of him and he instantly said, without hesitation, “Diana Ross.” [I said] “Boy, I couldn’t agree with you more, but why Diana Ross?” And he said “has there ever been a star who really is a superstar?” You could look at Celine Dion, Barbra Streisand and Stevie Nicks, but Diana had the glamour, she broke so many barriers as a black woman, she came of age during the ‘60s, she knew Nelson Mandela and Dr. Martin Luther King Jr., she was part of Motown’s success, she did movies and TV. This is the third time we’re having her and it’s just a great show. We’re so thrilled that she wanted to come back, so I’d put her up there.

[Also] John Legend, who has truly lived up to his last name. He’s somebody that has permeated, not only the singing and fabulous piano playing world, but also writing, producing and “The Voice.” He even chooses the endorsement deals and commercials he wants to do with a sense of cleverness, as does his wife [Chrissy Teigen]. He’s a family man and I think he’s incredibly special. He was also the very first artist who tweeted abo/ut how excited he was to be coming to Ravinia [back when Twitter just began].

I’m excited about Gladys Knight and Heather Headley. We’ve only had Heather once at Ravinia in the Martin Theatre. It was a great show. She’s a terrific artist from Broadway and clubs, and who doesn’t love Gladys Knight?

Ravina’s hosted lots of double headers over the years, but you have triple nights of Train. You must be very confident in their popularity.

Kauffman: That’s certainly our hope and we have had them a couple of times. Both were doubles and both sold out. There are people who may not choose their genre as much as they choose the night of the week they come to Ravinia: a Friday, a Saturday, a Sunday. We’ve got all three for them in this case. There’s something about Train’s infectious positivity and optimism and the hooks that get in your head and stay, but in a good way…To your point about triples in general, there’s only been one other triple in Ravinia’s history and that was Matchbox Twenty and the Goo Goo Dolls…

Which shows would you suggest buying tickets to instantly because they risk selling out?

Kauffman: I think Carrie Underwood’s a good example. There’s nobody like her. She was the one that broke Ravinia open to a whole different, [newer] strata of country artists…She’s going to do two shows, one with the orchestra and one with her band. I think we’re going to see not just a few Carrie fans that come to both nights!

John Legend, Sheryl Crow, Willie Nelson and the Train performances are really good examples. Lauryn Hill would be in that category. She’s only been to Ravinia once and it was one of the best shows of anything I’ve ever seen. The Beach Boys always do really well for us. I think Jesse & Joy opening our season. They’ve never been with us before and they have a huge following. Talk about infectious energy and appealing to younger audiences! Indigo Girls and Ani DiFranco is during Pride Week, plus Ani’s never been to Ravinia, so we’re very excited about that.

I think amongst our jazz aficionados, Tony Bennett and Chick Corea & The Spanish Heart Band with Rubén Blades are going to be very popular. I think there’s a lot of people who are rediscovering Rubén because of his important cameo moments in that recent Linda Ronstadt documentary film [“The Sound Of My Voice”] when he’s coaching her on [how to sing] in Spanish.

What are your hopes for Ravinia this season?

Kauffman: I hope that people come and enjoy the new RaviniaMusicBox. It’s a really cool thing that the Ravinia family and I have been talking about, working on and creating for 15 years, so almost my entire time at Ravinia. It’s a ticketed but free opportunity for people to get a taste, maybe a moment of seduction and enticement around classical music that’s a key part of what Ravinia’s always been. Maybe somebody’s there for the King Crimson show, they come, they get a good seat on the lawn, they have their picnic, they go to the gift shop, they look at the sculpture and they still might have a couple hours, so they go over to the MusicBox and they experience what’s there. I don’t want to go into a lot of detail on it because if I could really explain it, we probably wouldn’t have needed to build it. But it’s fun, it’s cool and it’s interesting, so I’m excited about that happening and I hope people avail themselves.

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For a complete list of upcoming Ravinia concerts, visit Ravinia.org.