SAN DIEGO — How funny is San Diego-raised singer and actress Andra Day, who performs here Friday, Sept. 19, with Jon Batiste at The Shell and who in 2021 earned both a Grammy Award and a Golden Globe for her searing portrayal of blues and jazz vocal giant Billie Holiday?

Just hearing the question had Day laughing with delight. She laughed even harder after being told by her interviewer that a recent AI search yielded the response: “Andra Day is not known for being funny … Her work focuses on emotional depth and powerful vocal delivery, not comedy.”

“Wait! You asked AI if I was funny?” said Day, who co-stars in the upcoming Bradley Cooper film comedy, “Is This Thing On?”

She burst into laughter again, then offered her own response to the question that had been posed to AI: “No, but yeah.”

Day grew more serious.

“It’s so interesting that you ask that,” she said. “Because when Bradley called me about doing (this movie), I was like: ‘What? I’m not funny.’ That was the first thing I said. And he was like: ‘No, I don’t need you to be funny. I actually need you to be serious and grounded, and I’m gonna make it so that it’s funny.’

“The character I’m playing, Christine, is a funny character because she’s very wise and caring. She is the person in the room that will always say what everyone is thinking, but that no one wants to say … She will tell you when you drive her nuts. There’s no questioning what Christine is feeling at any given moment.”

The same can be said of Day, whether she’s acting, singing or answering questions from the San Diego Union-Tribune, the newspaper she delivered to home subscribers as a part-time job here in her late teens.

Day threw herself, body and soul, into the role of embattled singer Holiday in director Lee Daniels’ Oscar-nominated “The United States vs. Billie Holiday.” Her gripping portrayal earned Day — whose given name is Cassandra Monique Batie — an Oscar nomination for best actress and a Golden Globe win. It was her first starring role in any film, following a brief singing role in “Marshall” in 2017.

Glowing reviews

The Washington-born actress and singer also was featured in Daniels’ 2024 film, “The Deliverance,” whose cast included Glenn Close and Omar Epps. Day also earned glowing reviews for her performance in director Titus Kaphar’s “Exhibiting Forgiveness.”

The release of both those films last year caused a ripple effect that forced Day to cancel her 2024 performance here at Humphreys Concerts by the Bay.

“I am so sorry I had to cancel that,” said Day, who opened her 2016 national tour with a show at Humphreys.

“There was so much going on, and I was trying to do a tour in the midst of doing promo appearances for two different movies and filming a third. I was like: ‘Guys, this is impossible.’ There were moments where it was scheduled for me to be in three different cities in one day.”

Day is now on tour with former “The Late Show with Stephen Colbert” music director Batiste. He won five Grammy Awards in 2022, including album of the year. His latest album, “Big Money,” features Day on the uplifting, gospel-tinged song, “Lean On My Love.”

A 2003 graduate of the San Diego School of Creative & Performing Arts, Day spoke thoughtfully and animatedly by phone from a Sept. 12 concert tour stop with Batiste in Oregon.

The topics she discussed included Batiste, their tour, her film work, growing up in San Diego, faith, romantic heartbreak, her upcoming singing gigs with a big band led by jazz bass great Christian McBride, her plans to make a dance-happy house music record, and more. The interview has been edited for clarity and length.

Q: If you think back to when you were attending the San Diego School of Creative & Performing Arts and working various odd jobs, including delivering The San Diego Union-Tribune.

Day: (laughs)

Q: What were your goals for the future at that point, and how close is the reality now to what you envisioned back then?

Day: Super close! I feel it’s a blessing to be able to do what it is I’ve always been passionate about and what I’ve always loved. Back then, my goals were the same. My goals have pretty much always been the same my whole life … I was very laser-focused on what I wanted to do, being creative and a performer and an entertainer. So, they’re definitely very close.

Q: Things have clearly worked out well.

Day: I wish some things would have been bigger. And there are some ways in which I far surpassed what I thought the vision would be. I love that kind of variety. I love that what I envisioned was different from what God envisioned for me.

Q: Have there been some good surprises along the way that you couldn’t possibly have anticipated?

Day: Yeah, for sure. Just the people I’ve been able to collaborate with, (including) one of my icons, Stevie Wonder, and to meet incredible people like Erykah Badu and Lauryn Hill. But more than anything, it’s been the way (my) music has impacted people. I don’t think I expected that. And that’s different from when I was young and doing a newspaper route. I was like: ‘I want to be successful in music, and I want to be famous.’

I didn’t think too much at the time about my music having an impact, how it could affect people’s lives and doing a song ("Rise Up") that’s become an anthem that’s been adopted by global leaders and global movements. I wouldn’t even have known how to envision something like that, so it’s been a blessing. It reminds me we have a purpose, and it’s usually greater than what we thought it would be.

Q: What were you thinking when you wrote and recorded “Rise Up,” which has become an anthem of self-empowerment, for your 2015 debut album?

Day: (laughs) To be honest, I was trying to get out of that (recording) session! I was tired and stressed out. I was probably aiming for going to grab something to eat afterwards. It’s interesting because, going into that session, I was very discouraged about where my career was, and I had got some not (good) news about some friends. I went and sat out in my car and I just prayed. I was like: “God, I don’t even want to be here, so whatever you want to say, or whatever you want to do, please just do it. And do it quickly!”

When I got back in the studio, Jennifer (Decilveo), the producer, was working on this chord progression. I was like: “All right, just play it, and I’ll freestyle something. Let’s see what happens.” And the majority of the song came out in that freestyle. After that, it was like, I forgot about (the song). It wasn’t until later that people at my record label said: “You should pay attention to the song you wrote.” And then, it was like: “Oh, wow.” Maybe I wasn’t in the right headspace to receive it, but (the song) immediately knew it was definitely supposed to be a part of the album.

Q: Your upcoming San Diego concert at The Shell with Jon Batiste will be your first gig here since before the pandemic. Do you have anything special planned?

Day: Yeah. The collaboration of myself and Jon’s band is special. There is a song (“Lean On My Love”) that we just released together for his (new album) that I’m very excited about, and it’s a message of love. John is a brilliant musician, artist and creator who is very impactful in the world. He is so committed to pouring love, hope and light into the world. So, that’s the goal. That’s what we want to do on stage.

And each night has been different, which has been really exciting. Because at each venue in each city, we all have a special experience. We’re very excited to see where the audience takes us.

Q: You and Jon have a great musical rapport. When you guested on his new album, “Big Money,” did you know you were going to be going on the road with him to tour it?

Day: No, but that’s very Jon! I also don’t know what I’m going to be doing every night when I walk on stage, but it’s cool for me. I haven’t toured in a while and this is an amazing way to dip my foot back into that world. I get nervous — I always have — every time I step on stage or get in front of a camera. But it’s such a good, exhilarating feeling on this tour to have that sort of looseness and that freedom. That is what we love as singers, as musicians, (that) we don’t know where things are going to go.

So, I did not know I was going to tour with him. But Jon is definitely one of those people, like Christian McBride, who is musically brilliant, and — whenever they call me to do something — I say: “For sure!” I can’t say too much yet about the project with Christian and his big band, but I am definitely excited.

Q: Some people believe that to write a great love song, you first have to have your heart broken at least once. What do you think?

Day: (laughs) I think: “I’m over that s–!” I don’t know. I think there is some truth to that, right? Because I think there’s just experiences in life that kind of sober us a little bit. The experience of heartbreak, and of any type of experience, can help you write any type of impactful song. But I think you can also experience heartbreak and not write a great love song.

Writing a great love song, about any type of love, the necessary requirement is truth — to be as truthful, authentic and candid as you can be. Being detailed and truthful is what allows people to write great love songs about any type of love, whether it’s romantic, familial, spiritual. How truthful can we be about ourselves, internally? That’s the main ingredient for writing a great love song, or a great song, period.

Q: Even though the inspiration is quite different, I would rank your (2024) album, “Cassandra (cherith),” alongside Marvin Gaye’s “Here, My Dear” as a classic breakup album…

Day: Oh, thank you so, so, so much. You’re gonna make me cry. I’m sorry. I’ll let you finish asking the question.

Q: The topics you address on “Cassandra,” as I hear it, include faith, vulnerability, heartbreak, hope, resiliency and self-acceptance. Am I accurate about that? And what were your goals in putting all of that into an album?

Day: Oh, my gosh, that was insanely accurate. Oh, my god, I love the way you listen to music because that was the journey. That’s what the album was supposed to be saying; that’s why I named it “Cassandra.” Because there are many facets to the album. Often times, when you do a song (of empowerment) like “Rise Up,” everybody just thinks you have all this wisdom. And I was like: “No, I’m really a mess quite often.” Sometimes, I have good moments and sometimes I have bad ones.

But the “Cassandra” album was made exactly to speak to that, to speak to resilience, and to honor the journey. You will not experience things that feel good all the time and you will not do things that are good all the time, although sometimes you will feel good and do things that are good. The only travesty for me is to not learn or grow, personally, spiritually, to not let all of those things grow you, transform you and prepare you for whatever the next season of your life is.

That’s why I ended the album with the song “Still,” because that song talks about being stuck in something and going around in circles. Like, I’m still stuck. I’m still in love with this person. I still feel miserable, I still am dealing with self-loathing, or whatever. “I’m still, I’m still.” And then, all of a sudden, you just allow yourself to go through that process, to get to a place of actual stillness, which is healthy for us. That’s what the album represents to get to this place of stillness and peace, and to accept it: “Oh, that was the journey.” And I should honor that, not resent it, not repeat certain things, but also use the lessons to grow me and to prepare me for the next season.

Because there will be a whole other set of lessons. So, it’s really about that process. And it’s about honoring that journey and who we are, and our ups and downs, our peaks and our valleys.

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