After persevering through “twists and turns” in his early days, the 12-time Grammy winner is still breaking records — and barriers — as he relishes a joyful family life

John Legend was on top of the world in 2018 when he became the first Black man to earn the coveted EGOT status.

Just a year later the 12-time Grammy winner made history again, adding three more letters to the designation — held by only 18 others — when he was crowned PEOPLE’s Sexiest Man Alive. “The pièce de résistance! I still can’t believe it,” says Legend, 45, the very first EGOTSMA.

Sharing his accolades with wife Chrissy Teigen, 38, has made his wins through the years all the sweeter. “She’s my best friend, she’s my partner, my lover,” says Legend, who’s dad to daughters Luna, 7, Esti, 15 months, and sons Miles, 5, and Wren, 9 months. “We’ve been together through it all.”

Below Legend, who kicks off a new leg of his “An Evening with John Legend” tour on May 31 and is featured on the cover of PEOPLE’s 50th special anniversary edition with 10 other Hollywood superstars, looks back on his early days hustling in the industry — and everything he’s built since.

I look back and I’m like, “It all worked out.” Even when things didn’t work out in the moment, it’s all led me to where I am. I don’t really have a lot of advice for my younger self. I’m like, “You’re going to mess up, and you’re going to figure it out.” Eventually I got to be on the cover of the Sexiest Man Alive issue, which I never would’ve dreamt of during this time.

All the twists and turns, all the ups and downs, all the rejections and me persevering through them is what got me to where I am now.

What do you remember about winning your first Grammy in 2006?
To get all the Grammy nominations was incredible and just mind-blowing. I was nominated for eight that night [and] won three of them. All of those things were things that I dreamt about when I was a kid. I wanted to be on that Grammy stage. I wanted to make a living making music. We went out afterwards. My family was in town from Ohio, and it was a party. I’ll never forget that night.

Who are the artists your kids are really excited about?
Well, my son, his favorite artist is John Legend [laughs]. His first love has been my music, but now that’s expanded to Usher. Miles loves Usher as well. He just likes a lot of voices that are soulful. Then Luna, she likes pop, and she likes female singers a lot. Her mom and her both love Ariana Grande, Beyonce, Rihanna, Taylor Swift, of course. One of my favorite newer artists is Olivia Rodrigo. I really love her songwriting. It seems like she’s so self-aware and writes with such heart and such depth, and just is so reflective of what it means to be a real artist.

Another younger artist that I got a chance to work with and do a song with recently is Jacob Collier. He’s just a musical genius, and the things he’s able to do musically, you’re just like “How is that even possible?” He takes music in so many interesting and different places. We did an amazing cover of “Bridge Over Troubled Water” with Tori Kelly.

In 2014 you launched the FreeAmerica foundation. What’s been your priority when it comes to the fight to end mass incarceration?
All that we’ve done with FreeAmerica started with listening, started with meeting people where they are, hearing their concerns and seeing how we could be helpful. I’m so grateful for the work we’ve been able to do, all the partners that we have, and that we’ve made real progress. Since we started incarceration has gone down about 30 percent in America. We’re not the only ones working on it, but we are in the fight, and there’s so many other people fighting with us.

They say hope is strategy. That means you have to have hope to drive you to keep working, drive you to keep thinking about how to make the world better. I’m continuously hopeful that even when we have backlash, even when we have politicians who want to be tough on crime all the time and don’t think about justice and mercy… Even when we have that, we keep fighting. We keep speaking up for what we believe is right. We’ve seen real progress from it.

Take me back to when you first met Chrissy. You’ve said before you were taken by how funny she was.
My friend Nabil Elderkin wanted to shoot a video for a song called “Stereo.” He really wasn’t directing music videos yet, and he wanted to show people that he could. He cast this young lady named Chrissy Teigen that he had shot before for another campaign.

As soon as I met Chrissy, she had this infectious laugh. She just lit up the room. When she met me, I think I was shirtless ironing my own clothes because we didn’t have a stylist for the shoot. It was very low budget. I styled myself, ironed my own clothes. She walked in, and that’s how we met. I’m sure she made a joke about that. We just clicked right away.

John Legend for PEOPLE’s 50th anniversary issue.ART STREIBER

“All of Me” took your career to another level when you released it in 2013. How do you feel about it now?
You never know what’s going to happen with songs. Obviously it ended up being my biggest song, but it took a long time. It came out in, I believe, August of 2013 and it didn’t hit No. 1 on the charts until, I think, May of 2014. People ask me if I ever get tired of singing certain songs that everyone wants to hear, and I’m like, “No. I’m grateful.” I’m grateful that this song has had this much impact.

Nabil Elderkin, the same guy who directed the video where we met, was the director of this video as well. We shot it the same week we got married at Lake Como. We went a little bit early and shot the video on the Thursday and Friday before we got married. We finished the shoot, got ready for our rehearsal dinner, and then the next day we got married. It was a very full-circle moment. Then of course this song goes on to be the song that everyone plays at their weddings.

What was the best part of renewing your vows last year in Lake Como with Chrissy?
We went right back to the same place where we got married. We had just completed our family just a couple of months before that, and we got to bring all of them to Italy, to Lake Como where it all started. It was such an amazing celebration. We recreated the magic of our wedding night.

One of the things we wanted to make sure we did was to really be in the moment. We were so emotional being there with our kids and knowing that we could celebrate our love with the products of our love.