Presented by GRAMMY.com, Living Legends is an editorial series that honors icons in music and celebrates their inimitable legacies and ongoing impact on culture. GRAMMY.com recently caught up with multi-GRAMMY Award winner Herb Alpert, whose work as a bandleader and label head have put him at the forefront of jazz and instrumental music for decades.

Herb Alpert is the "A" in A&M Records (along with "M" Jerry Moss), the legendary label that was home to the Police, Cat Stevens, Quincy Jones and Alpert’s own prolific recording career as a songwriter, trumpet player and leader of the Tijuana Brass.

A towering list of accolades — 14 platinum records, nine GRAMMY Awards, a 2012 National Medal of Arts award from President Obama, for starters — don’t necessarily hint at the equitable and unpretentious man behind the music.

"I'm making music for myself. And when I feel good playing it, it gives me energy, I feel great about it," the 87-year-old trumpet player tells GRAMMY.com. "If someone else happens to like it, it's a big win for me."

Alpert's songs — including "This Guy’s In Love With You" (his vocal debut and a No. 1 hit), "A Taste of Honey," "Spanish Flea" and "Ladyfingers" — are woven into the fabric of society, helping Alpert sell more than 70 million records (numerous Tijuana Brass songs were used as theme music for the ABC TV show "The Dating Game!").

His 1965 album Whipped Cream & Other Delights remains a staple in millions of homes, thanks in part to a comely model "dressed" in whipped cream on the cover. Releasing more than 40 albums since 1962, including the No. 1 charting gold-sellers Whipped Cream…, Going Places, What Now My Love, Sounds Like...and The Beat of the Brass, could easily allow the prolific trumpet player and businessman to rest on his considerable laurels.

However, Alpert’s creativity and philanthropy continues unabated. His generous support has allowed students at UCLA, CalArts and the Harlem School of the Arts to follow their love of music. The artist’s own verve and pursuit of personal creative satisfaction continues to drive him daily, whether he’s painting, sculpting or making music.

Alpert spoke to GRAMMY.com from his California home studio, discussing his most recent album, Sunny Side of the Street, how he approaches cover songs, painting and sculpture, along with opinions about how music and art should "grab you."

Nice to see you, thanks to the magic of technology!

Well, it's great when you have a 5-year-old around and they can help you! This is a little aside, but I was just totally shocked two weeks ago because somebody on TikTok picked up one of my songs. The song [he hums it] "Ladyfingers," they picked it up, put it in a little vignette video. It went viral on TikTok. It was written by Toots Thielemans from an album that I did 55 years ago, Whipped Cream. So far, and it's almost embarrassing to say this, but it had 100 million streams, this one song. I mean, it's like unheard of!

That number is incomprehensible, isn't it?

I mean, especially for me. I started in this business with a wire recorder. This was before tape recorders! I've never been on TikTok. I don't even know how to get onto it.

Let’s talk about your latest record, Sunny Side Of The Street. I love your take on "Going Out of My Head." I first heard the Zombies' version; what was your goal when you decided to cover it?

Whenever I do a song that's familiar to others, I try to do them in a way that hasn't been done quite that way before. I think this was in the midst of the pandemic and I was isolated in my house. I was thinking most people are going out of their head right now trying to figure out what to do. Wear the mask, don't wear the mask, information was flying by us.

I just started playing this song, then at the end, this end vamp that I do I kind of went a little off on the horn — music from an insane asylum. [Laughs] It's impressionistic is what it is, I wanted it to feel like, yeah, it's possible to go out of your head and still retain some sanity.

The notes I made about the song were "spooky craziness."

I see music as impressions through the horn. That's the way I try to do it. I'm basically a jazz musician, and I don't plan it, I just do it. You know, when it feels good I stop. This is a little strange to say, but I'm not making music for anybody else. I'm making music for myself. And when I feel good playing it, it gives me energy, I feel great about it. If someone else happens to like it, it's a big win for me. But that's not my goal. My goal is to make music that gives me a feeling of satisfaction, that I did something that feels right for me.

In one recent live review, the journalist said something along the lines of "Has any instrumentalist reached such a broad swath of people?" I’d have to say no, and wonder why the popularity of instrumentals waxes and wanes.

Well, there's a period where trumpets were in vogue, after [1962's]  Lonely Bull. Trumpets were on the radio, and then all of a sudden, we got closed out. Even though radio is very slim and there's other ways to expose music, there's certain music that the programmers like and for the most part, it's not instrumental music. So timing does play a huge part in the success that I've had, and I am very grateful for that.

"I'll Remember You" was done by Don Ho, Andy Williams and Elvis Presley… and now you. I feel you must know those three greats.

Well, I know the guy who wrote that song. Kui Lee. Unfortunately, he died when he was about 34. When I played in Hawaii at the HIC with the Tijuana Brass, after the show I went to see Don Ho at the International Marketplace. I had a couple of tropical drinks and I had my horn with me. Don started playing this song and I loved the song, the melody, everything about it. I got up on the stage and started playing that song with Don Ho.

My partner Jerry Moss was with me. It was unfortunate that we didn't have iPhones, so we couldn't record it. But I've always thought about that song. I got a call from Jerry about eight months ago. He says "why don’t you record ‘I'll Remember You?’" I wanted to do it for Jerry, because he was so instrumental in my success as an artist. So I recorded it. All of a sudden, I was getting that feeling of wow, this is good. This is a nice tribute to a wonderful writer" who unfortunately didn't get a chance to realize the success that he had.

I can listen to that [song] for my own pleasure. And what I've learned to do through the years as an artist, is I learned to become an audience to my music. When I do a recording and listen to the playback I'm not listening to the trumpet player; I'm listening to the overall feeling of what it says. I judge it like I'm an innocent bystander. I don't know how all of a sudden this technique got to me, but that's the way I do it.

When recording technology began advancing and digital methods came in, were you an early adopter? Where do you stand on technology?

I like it; in the right hands, it’s great. In 1979, at our A&M Studios, the 3M Company loaned us one of the multitrack machines, a 32-track machine. I wanted to experiment with it to see if it was worthy of buying for A&M. On that session, I did "Rise." Strangely enough, I loved the recording; it was that live in studio. When we were ready to mix, the machine ate the first eight bars! So we had to reproduce that.

It's not the same experience that we had the ‘60s with gathering musicians in a studio and all working something out live. But given that the proper thought is there, you could come up with something…

Well, first of all, look: I think all art, whether it's acting, being a sculptor, painter, musician, poet, it's all about feeling. It's the feel that you get when you listen to something, and the beauty of it is you can't identify what it is that you like about it. The closest I've come is playing with Louis Armstrong one night. And the sound that was coming out of Louis’ trumpet was Louis Armstrong's personality. Period. It was him. It was just the guy I met who was lovely, who was smart, who was creative, and it was right there. That's the goal I think, for all artists, is to find your own voice, your own way of doing it, your own stamp. That's what I believe all artists should be looking for.

Yes, that certain "je ne sais quoi"…

I tell this story of standing in front of a Jackson Pollock painting. I tried to analyze it trying to see what his motivation was. Or, does it fit the title or blah, blah, blah. You won't get it. You have to just let it seep in. And if it grabs you, it'll grab you. If it doesn't grab you, that's the way it goes.

In terms of your own painting and sculpting, how did you begin?

I was traveling around the world with the Tijuana Brass in the ‘60s and used to go to museums. I kept seeing a black painting with a purple dot, or a white painting with a green dot. I'd look at the paintings and say, "why is this hanging in a museum?" I grabbed some canvases when I got home from tour. I started moving colors around with acrylic paint, like a monkey, just kind of pushing it around to see if I could get it into a shape that pleased me.

I got one painting that I thought was really good. I finished it at night, hung it up, and was anxious to see how it looked in the morning. I rushed down to look at the painting and it was almost gone, because I didn't prepare the canvas properly. I’d watered down some of the paint;  you can do that to acrylic paint. And the paint kind of seeped into the canvas, and it all but disappeared. So I started to learn more about how to do it.

I was having an enormous amount of fun painting. Like a kid in a candy shop. I've been doing it for more than 50 years, and had some great success. I’ve had shows in different parts of the world. Sculpting came in about 40 years ago. I’ve got all sorts of great pieces at museums in Chicago [Field Museum], New York, the Tennessee State Museum in Nashville.

Do you listen to music when you paint?

Sometimes, yeah, I like jazz. I think what's so beautiful about being an artist is what it proves to us is that there's beauty and freedom, and we have a freedom in this country that's extraordinary.You can do what you want to do. It might not be what other people particularly like, but it's free. Jazz is about expressing one's own freedom.

We saw the effect it had worldwide when Louis Armstrong and Duke Ellington used to go to foreign countries and they were treated like royalty because the people felt that freedom is special. And we don't want to squander it here. The heart and soul of this country is based on music and art. And we have the freedom to do what we want to do as artists.

A lot of your philanthropy involves music education. When you speak to a student or small group, what do they most want to know from you?

They always want to know what the secret of my success was. I'm passionate about what I do. If they're not passionate about wanting to be a musician, forget it, don't do it. Spotify [in particular] gets 100,000 pieces of music each day. Try to break through that maze! That’s crazy. So don't do it because you want to be famous, or you think you're gonna make a lot of money or attract women or men or whatever it is. You gotta do it for the right reasons. There are a lot of great musicians who never get heard. It's rough out there. If you're doing it for the right reasons, always have a backup plan, have something else that you can fall back on in case it doesn't quite work out the way you would like it to.

What was your backup plan? Did you ever have a day job?

No, I never did. I was lucky in high school. We had a little band and I was earning a living starting when I was 16 years old. We were playing for parties and weddings, making enough to survive. My backup plan? Boy, that's a good one. Don't do as I do, do as I say! [Laughs.]

You told me that success is really internal, but is there an award or laurel that means the most to you?

I guess finding Lani [Hall, once the lead singer of A&M group Brasil ’66], my wife, is the biggest reward award I've ever gotten. We've been married 49 years. And that's a key ingredient. I think love is crucial. She's my best friend and I couldn't be happier.

She’s often your musical partner as well.

And we’ve got dates through 2023. We’ve got London; we're playing at the famous Ronnie Scott's place in June ’23, playing there for a week and they're sold out. It’s a great feeling to know that the music I've made through the years touches a lot of people and man, I'm very grateful for that.

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