In 2024, singer-songwriter Andy Grammer was in the middle of doing Greater Than, a one-man show largely focused on grief and his own experience with losing his beloved mother, children’s music artist Kathy Grammer. “That was really, really special,” he reflects. “What’s so cool about it is there’s different items onstage and then there’s six phones in the audience, and people write down someone they love that has passed. And throughout the show I will take out a name and read it, and then the person will stand up and go to a phone and we’ll have a conversation about the person that’s passed away. Wild, awesome show — deep tears, crying, laughing, singing.”

But then, just when Grammer was wrapping up that emotional and vulnerable experience, he got a call from The Masked Singer, offering him the chance to theatrically perform songs by the Darkness, Post Malone, Jet, and George Michael, disguised as disco darling Boogie Woogie in a glittery purple leisure suit and perpetually smiling Muppet-face. “I was like, ‘Honestly, that sounds like a great pivot,’” he chuckles. “I thought that he was a fun character to inhabit for about a month.”

Grammer didn’t win The Masked Singer, placing second to Gretchen “The Pearl” Wilson. But judge Jenny McCarthy-Wahlberg unofficially declared that Season 13 had two champions and said Grammer “embodied this character.” So, clearly Grammer, who is officially the No. 1 Happy Pop Artist globally on Spotify, is winning at life.

While Grammer’s seemingly boundless cheeriness on anthems like “Keep You Head Up,” “Don’t Give Up on Me,” and “Good to Be Alive” have caused some critics to dismiss him as a fluffy artist, anyone who’s seen Greater Than; listened more closely to the nuance in Grammer’s lyrics; or checked out his many interviews about mental health and grief knows that he’s a deep guy behind his smile — and behind Boogie Woogie’s smile. “Coming from me, I think that talking about mental health could have an extra punch, because I’m seen as so happy,” he explains.

Following The Masked Singer Season 13’s grand finale, Grammer chats with me about why writing a happy song, while maybe not “cool,” is much harder than creating darker music; why “grief is an under-discussed topic” but “can be a really sweet door into unbelievable situations”; and how he developed a thick skin and stopped paying any mind to his detractors.

“Uplifting music… if it has intention and it’s grounded, then it’s a grounded optimism. I love the sound of that and when I’m in that lane, I don’t care what anybody says,” Grammer says, adding (with a smile, of course), “Everybody can screw themselves.”

LYNDSANITY: I’m excited to speak with you. I’m not happy you lost, but you didn’t lose. Jenny McCarthy said there were two winners this season, and I fully agree.

ANDY GRAMMER: Yes, two winners! I’m just holding onto that, putting that in my pocket.

But I’m happy because I’m talking to the No. 1 Happy artists on Spotify, and I’m happy that you got to the finale. On The Masked Singer, you said that you wanted to show that positivity and sincerity could win. You also talked about people would call you naive or critically dismiss you because of your cheerful attitude. I’d love your take on that, because why is it only “credible” if you’re singing about your misery all the time? We need both sides of the musical spectrum.

We need both sides. I don’t know, I don’t want to sound like something lame, but I think it’s really hard to write a positive song. I just think it is. I think if you sit down at piano and you play happy chords, it is much quicker to lean cheesy than if you just play dark chords. And so, there’s a skill, and then a straight-up perseverance to just write so many that you get to pick the ones that actually connect and feel grounded. There’s something about being too happy that can sometimes feel ungrounded, which I respect and understand. But we all need some positivity and to be uplifted from time to time, for sure.

Who’s the No. 2 Happy artist on Spotify?

I have no idea! [laughs]

I think it’s interesting you wore this Boogie Woogie costume that had a smile on his face at all times. I wondered if there was any significance to that, because you’re known for being this happy guy, but also, especially in recent years, you’ve talked very openly about your mental health. So, was there some kind of symbolism there, like smiling on the outside but not always on the inside?

Well, they tell you what your costume’s going to be. You show up to a Zoom meeting and they show it to you and go, “Is this cool?” And I’m like, “That’s unbelievable!” I really appreciated it. I thought that he was a fun character to inhabit for about a month.

As I mentioned, in the last few years you’ve done a lot of podcasts and interviews about mental health and going to therapy, and I think a lot of celebrities that used to never talk about that stuff now do talk about that. So, I’d love to discuss your mental health journey in the public eye. Why did you start to feel the need to talk about that?

Well, I think there’s room for both to be true. I think that sincerity and kindness and being uplifting does have a space and can win. And then also coming from me, I think that talking about mental health could have an extra punch, because I’m seen as so happy.

When you started to discuss mental health, how was the reaction from your fan? Were they surprised?

It’s been really sweet and sincere. I think that it’s a different world than I grew up in right now, and there’s a lot more things coming after your mental health that maybe weren’t when we were growing up. It’s just kind of the norm, with all the screentime and all the extra things that are coming at you all the time, to understand that it can be talked about and it’s OK to talk about it.

And you’re a parent; one of your daughters, very adorably, called in to the show. Do you worry as a parent when you’re thinking about mental health? Like you said, it’s a different world now. What are your concerns for your kids and for the younger generation in general?

Yeah, I think that with the phone stuff, it can be all day long. Unless there’s guardrails, there can be not enough time to just be. And so, I think talking about it, being intentional about it and figuring out spaces where you can take care of your mental health and create some space to be “bored” a little bit — I definitely am thinking about that a lot as I’m raising my two little girls.

How is all the stuff we’re talking about now — the world in general, but also you becoming so open about your mental health — affected your songwriting? Is it more happy, less happy, or about the same?

Well, I think that the secret to writing a happy song that works is being grounded. If you just go like, “Everything’s good, the world is amazing,” some people are like, “I don’t believe you.” If you go, “I’m having a really hard time, but even so, let’s be happy,” that starts to be something people can hear. Almost a rebellious sweetness.

What would you say is your absolute happiest song?

Well, it’s funny, because one of the ones that does the best is a song called “Don’t Give Up on Me” – which, I don’t know if that’s happy, but it leaves you feeling hopefully encouraged or inspired. So, the word “happy” gets a bad rap, I think.

What you’re saying reminds me of an interview I did with OMD. They’d done some more experimental music because they wanted to appeal to critics, but then they’re known for these very bouncy new wave hits. And the lead singer, Andy McCluskey, told me writing those bouncy hits was much harder than noodling around and doing the “weird” techno stuff.

There’s something very vulnerable and putting yourself out there to, yeah. There’s something vulnerable about writing a happy song. It just is. It’s just not as “cool” to start with major chords. It just isn’t, in my opinion.

Obviously, if you’re the No. 1 “Happy” artist on Spotify, then you’re doing something right. But did the criticism when you first started out bother you at the time, or make you think you needed to shift course?

I think so. I think no matter what, whether you’re an indie artist, you want a pop hit; if you’re a pop artist, you want an indie hit. You always want whatever you don’t got, but then hopefully you just continue to get more and more clear on what you love. There’s the Rick Rubin book The Creative Act where he talks about the hardest thing is to make things that you love. Getting yourself attuned to what you love is so much harder than that sounds. It sounds like, “Well, why don’t you just make what you love?” It’s like there’s all this noise going on all over the place to block it all out. So, be like, “Wait, what do I love? Let me try to make that.” That’s a skill that I think you hopefully get better at and have to struggle with your whole artistic career.

Since you come from a background where your parents did children’s music, have you ever done children’s music, or wanted to?

I haven’t done a children’s album. We just watched Captain Underpants with my kids last night and I have a song in that movie and I have a song in a Curious George movie, and so there’s a sweetness to writing something simple that children can sing. That is great. And my song “Don’t Give Up on Me,” one of the big reasons that it went big was I did it with an elementary school choir. Something about children singing, “Don’t give up on me” is just so beautiful.

You talked about your mother Kathy on The Masked Singer, and you’ve talked a lot in interviews about your grief when she passed. I’m so sorry for your loss. Do you have any stories about fans going through similar situations who have resonated with what you’ve said about your grief experience?

I think that grief is just an under-discussed topic. I think a lot of people don’t really know what it is or how to talk about it, and a lot of times we just go to a funeral and then move on. But it can be a really sweet door into unbelievable situations. So, the way that I understand grief is, how you keep someone alive in your life is by doing acts of service that you do in honor of them. And that has been such a beautiful part of my life. And so, writing music with my mom in mind, or talking about her, or doing acts of service in her name, has been one of the most fulfilling parts of my life, for sure. … A lot of times I’ll donate in her name. There’s a hospital in Ohio, because of how many times I went to that hospital, there’s a room with her name on it, which is really sweet. And then thinking of her, she was a songwriter as well. I just did a one-man show last year, which was all about grief.

Oh, wow.

It was wild. And there was spoken-word poetry and there were songs and there was a lot of talk about her that was honoring her for a whole tour, which was really special. … I think we’re going to do it again. It’s called Greater Than, and it was a one-man show that was really, really special. What’s so cool about it is there’s different items onstage and then there’s six phones in the audience, and people write down someone they love that has passed. And throughout the show I will take out a name and read it, and then the person will stand up and go to a phone and we’ll have a conversation about the person that’s passed away. Wild, awesome show — deep tears, crying, laughing, singing, everybody going nuts. So, I was finishing that show when I got the call to do The Masked Singer, and I was like, “Honestly, that sounds like a great pivot, like a wild new experience, so let’s go do that.”

I was about to ask being on a fun show like The Masked Singer and getting to wear this crazy costume was good for your mental wellbeing. It sounds it was!

Yes, it was a hard reset on what I was doing.

Going back to that smiley Boogie Woogie costume, as I said, there are some people who think you’re a goody-goody and they don’t like that. But then, of course, there are lots of people who really resonate with that. Have you ever felt pigeonholed, like, “Hey, I’m not just the happy guy all the time”? Or did you ever feel any pressure, like, “OK, I have to write another happy hit”?

Well, my first song that came out that did well was a song called “Keep Your Head Up.” That came from being a street performer and my mom had just died, and I wrote myself a song. So, if it’s grounded in something real, then uplifting music is — I’m not going to curse! — awesome. If it has intention and it’s grounded, then it’s a grounded optimism. I love the sound of that and when I’m in that lane, I don’t care what anybody says. I don’t care. Everybody can screw themselves.

I know you were a busker on Santa Monica’s Third Street Promenade before you were famous. You were such a great entertainer on The Masked Singer, and are in general, so I’m wondering if busking honed your performance skills and trained you to win over audiences.

I think of all the art forms, standup comedy has got to be the hardest one, because every couple seconds if there’s not a laugh, it gets so awkward. And I think that street performing is the closest that music gets to that, where you have to just go, “I’m going to shout to try to build a crowd and I’m going to sing, and if you don’t like it, it’s going to be really awkward. Here we go, let’s do it!” And just doing that for eight hours every day will get you to a place where you don’t care that much. You’ve trained yourself that if someone doesn’t like what you’re doing, you’re going to be all right, everything’s fine. And learning that skill was really important for the career that I have, because people are going to like you or they’re not going to like you. One of my favorite things is I’ve done the national anthem, so many times for sports events. I’m like a huge sports fan, got to do the NBA finals, NHL, NFL, college, the World Series. And when you were putting yourself into a place where people [in the crowd] didn’t ask you [to perform] and large numbers are watching you, then I go to my Twitter and I have a text-chain with all my high school basketball team, and I just send the meanest [tweets]. And we just die laughing together about it. So ,you develop a skill to where it doesn’t all go in so deeply. It’s just not that serious.

That’s an important skill to have! And the national anthem is not an easy song to sing. Did you do covers when you were on the Third Street Promenade, or did you do your own songs? And were any covers that you ended up doing on The Masked Singer?

None of the covers made it from there to here, but I do remember there’s something really valuable [that I started out] singing a ton of covers, because you are, every day, looking at the mechanics and singing the mechanics of what makes a great song. So, I was studying a lot. I hadn’t been singing [in my recent career] as many covers as I just did on The Masked Singer, so that opened me up again to when you sing something, you’re like, “That sounds great. Why?” And then you go deep into, “Why is this song so good? Why is this pre-chorus lifting off into the hook this way?” It gets almost scientific about it.

You threw down the gauntlet in your first episode, because you did the Darkness’s “I Believe in a Thing Called Love,” and Justin Hawkins’s voice is so high. And you nailed it!

Yeah, I chose that one because I wanted to come out hard and ridiculous.

It’s pretty cool. What I also think is funny is that Rita Ora later claimed she didn’t know the name of the lead singer of the Darkness, when she was on the U.K. version of the show when he was revealed. She knows his name!

Oh, she knows it. Got it.

I don’t mean this in any kind of shady way, but I don’t think a lot of people necessarily realized you have that crazy range as a singer. Was that something you wanted to sort of flex?

I think also it’s been something I’ve really developed over my career. When I started as a street performer, I didn’t think my voice was very good, and sometimes our weaknesses are very important. I remember when I was street performing, I was like, “It’s not going to be my voice that does this. I’m going to have to write songs. I’m going to need to really figure out how to write songs, because I’m out on this street and I can tell I don’t have the best voice out here.” But over 15 years of singing every day, there was something sweet about going on The Masked Singer and being like, “Oh yeah, my voice is pretty good now! This is going to be fun!” I had that exact thought, literally — almost surprised.

The judges were so complimentary. They guessed you were great vocalists like Darren Criss, Brandon Flowers, Josh Groban, Mika, and Adam Lambert. That must have felt good.

Yeah, just stroking my ego behind a monster mask [laughs]. I loved it!

Since we started off with talking about any kind of stigma about happy songs and how they’re deceptively not easy to write, my last question for you is: What’s the key to writing a good happy song? If there’s someone watching or reading this who’s like, “I want to write the happy anthem of 2025,” what’s your advice?

I think that it has to be true. And that sounds maybe lame, but again, I’m singing, “You gotta keep your head up to myself” when my mom just died. I don’t know why that transfers to then everybody really getting it, but the intention of it is true, therefore that works. So, don’t [try to] write a happy song. Don’t fake it. I think that people can smell bullshit on happy songs way quicker than on sad songs. That’s what I’ll say.

And hey, you cursed after all! [laughs] So, we’ll end it on that note. Congratulations on being, in my mind and in Jenny McCarthy’s mind, the co-winner of The Masked Singer’s lucky Season 13.