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Singer-songwriter Jewel brings her Handmade Holiday Tour back to the Ridgefield Playhouse on Dec. 4.

Singer-songwriter Jewel will return to the Ridgefield Playhouse on Dec. 4 as part of her second annual Handmade Holiday tour. She will be joined on stage by her son, father and brothers as they perform holiday classics and, of course, Jewel's biggest hits.

What can everyone expect from the Handmade Holiday tour?

I’m bringing my family out with me. My family’s from Alaska. They’re actually on a hit TV show called Alaska: The Last Frontier on the Discovery Channel, which has been really fun for me because the world gets to see how I was raised. I’m bringing my dad and my brothers out with me and my son. It’s a chance for my son to be around my family, be part of music as the culture. I was raised making gifts for my family, because we didn’t have the money to buy gifts. And so I wanted to bring that in as part of it. The doors open early and there’s a craft fair and my dad has made a bunch of handmade gifts from Alaska. My son is currently making as many bath bombs as he can. And I make jewelry (songlinesbyjewel.com) that people can buy.

You’ve always done an incredible amount of charity work. In August you made a speech in New York where you said you don’t want to make your next album, you felt compelled to make it. Do you approach charity and music in the same way?

Philanthropy for me is just how my heart is wired. I think it’s what makes a singer-songwriter different than songwriters. They have to have a heart for society. They have to care about holding up a mirror to society and giving it a voice. For me, philanthropy — because I did struggle so much, because I did have a difficult and abusive background, because I was homeless, because I know how much people suffer and struggle, I’ve always felt a duty to help because I know what help means.

The single greatest performance of your career, and this is a fact, was when you did “Silver Nickels and Golden Dimes” (a song written by a sixth-grade Howard Stern) at his birthday bash in 2014. How did that come about?

I avoided his show for so many years because I had to deal with a million rip-off artists and shock jocks in the ’90s just being brutal with me. So I always avoided Howard until I met him backstage one time and realized what a smart and intelligent person he was. And so I’ve done two interviews with him and they’ve been some of my favorite interviews. He asked me to do a song he wrote, and at first I was like you’ve got to be kidding me. So I just did my own interpretation of it. For his birthday bash he asked me to sing it and we’d become good enough friends at that point that I was totally down. I like really challenging gigs.

You said it was the “suckiest crowd” you’ve ever been around.

I think I said that on stage. I had to do something to get people to pay attention, because people were really talking a lot. Part of it’s because Howard was doing a live broadcast and you couldn’t really hear that well. But there were amazing performers doing amazing things on stage, and I’ve never been background music. I’m very prideful. Even when I was home singing on street corners I did whatever it took to get people to listen. And I’ve always been that way. When I toured with Bob Dylan, the reason he ended up meeting me and mentoring me was because I was kicking people out of his shows for talking when I was opening for him.

One more Stern-related question. You covered “Eleanor Rigby” for the Revolver 50th anniversary special they put together for his SiriusXM channel. You said it was a “tall order to tackle one of the classics.” What goes through your mind when you’re considering which songs to cover?

I never would have done that for anybody but Howard. “Eleanor Rigby,” when I found out that was available, I really felt like that was the most suited to me because it’s really quirky. But figuring out how to reinterpret those are really difficult, because you really have to change them and make them your own. Because you’re never gonna beat the original. They did it. They’re the Beatles.

When you first made it big, how do you wrap your head around what’s happening to you during something like that?

When I got signed I was quite afraid of fame, because I didn’t think I was psychologically built for it, just because of my background and the trauma that I had. Fame doesn’t change you, it exaggerates you. So if you’re insecure, you get more insecure. And that’s why you see so many celebrities self-implode. I know I was a real candidate for that. By the time I was on the cover of Time magazine, I couldn’t personally handle that. It wasn’t at a psychological pace that was good for me. I just started doing what Dylan and Neil Young taught me to do, which was follow my muse, and I began changing my musical styles, experimenting and just keeping myself interested and alive and curious creatively. I’ve always been going for a 50-year career. I know nothing is huge forever. I hope to keep a core fanbase that are singer-songwriter fans and I hope to be able to do this for 50 years.

This article appeared in the December 2018 issue of Connecticut Magazine. Like what you read? You can subscribe here, or find the current issue on sale here.

Mike Wollschlager, editor and writer for Connecticut Magazine, was born and raised in Bristol and has lived in Farmington, Milford, Shelton and Wallingford. He was previously an assistant sports editor at the New Haven Register.