“I’m not comparing what we do to teaching chassidus,” Benny says, “but at some point, you confront the power of the Alter Rebbe’s mashal. To teach, to uplift, you sometimes have to do things that are different from what you’re used to, to reach into new places. Who knows how much powder is needed to create life?”

Benny was addressing a claim recently issued by an Israeli radio host: that Benny Friedman had forgotten his early influences, the music of Nichoach — Chabad’s music production company — and forged a new path, producing music that was foreign to his origins and mission.

To understand his answer, you have to understand the trajectory of Benny Friedman’s career.

The proverbial child born at the top of the mountain, Benny had the right yichus, voice, and background to segue effortlessly into a singing career. He was the sort of kid offered the mic as a matter of course. He davened for the amud on the Yamim Noraim as a bochur, and just after his wedding, he released an album that showed him walking boldly between the painted lines on Eastern Parkway, his expression promising to take a bit of yesterday and mix it with a bit of tomorrow to create something special.

He stepped nicely into the spot cleared for him — Avraham Fried’s nephew , chassidic warmth, brilliant smile — all the sweet elements of a 2009 superstar. The album was a stunning success, but nothing close to the follow-up: Yesh Tikvah was released in 2012 and suddenly, every other singer was scrambling to cobble together hopeful Hebrew words.

There was a dreamy period between relative obscurity and success when Benny Friedman was the unquestioned new star on the music scene. But then came the next chapter: Without the bounce of the young, new, and unexpected, he was just the establishment singer, no longer the new guy. The shift wasn’t felt just in terms of audience perception, but also in a very practical way.

“I started when I was just married, what did I need? The world was wide open, the road stretching out before me. All I had to do was sing. It was glorious!”

Then life happened. One child, then another. The apartment was too small, the travel schedule exhausting, the late nights difficult — and the grind of predictability set in. Standing on stage every night wasn’t so much fun anymore. Singing as full-time parnassah takes determination, toil, and focus.

Benny has a way of speaking to the point, opting for the quickest verbal route from point A to point B. “If we’re being candid, it’s not just that you need to keep busy to stay above water financially — there’s something else.”

He pauses, but just for a moment. “In the frum world, there’s a certain aura of celebrity around singers, that’s just how it is. So you can’t just be a plain guy, another one negotiating for tuition breaks, you know what I mean?”

He recalls going to lease a car. “And the guy meant well, he wasn’t being pushy, he says, ‘Listen, this is a fine car, but it’s not a “Benny Friedman car,” it’s not on the level for you.’

“And that,” the singer says emphatically, “that can derail you, the idea that you’re somehow different, more. The yetzer hara is real.”

Benny Friedman wanted to try something different — to be a regular guy and also a singer, to somehow keep the baby and the bathwater.

Around him, the traffic grew dense.

His style, classic chassidic music, had its loyal following, but there were different sounds too, new sub-genres pulling at the edges of the Jewish music tent.

“Look, it’s a good thing. Not just because parnassah is from Hashem and everyone gets what’s intended for them — though that’s a reality, a metzius. It’s also that rising tide lifts all ships” — he stops and his eyebrows go up, “did I get the expression right? Whatever. You know what I mean, the more engaged the audience is with Jewish music, the better it is for all of us.”

Faced with a growing field of competitors and musical styles, Benny had to look in the mirror and figure out who he was and what he wanted to sell. Not to build the brand, or rebuild the brand, but to decide which boat he would be riding through the tide.

“You know, the middle of a career is a hard place to be,” he says. “At the beginning, there are no expectations and whatever you do is a pleasant surprise. The challenge is once you create an identity, so people say, ‘Okay, that’s just Benny.’ My last albums were successful, people liked them, but they didn’t have the magic of the first two, they weren’t groundbreaking. That was the feedback: I was producing more of the same. And I know that to stay relevant in this business, there needs to be magic.”

Just about a year ago, this past January, Benny was invited to Memphis. A local family, the Kahanes, were hosting a public community concert in honor of their daughter’s bas mitzvah, and they asked Benny to sing.

He sang like he was far from New York, letting his voice go the places it wanted to, connecting with an audience thrilled to be experiencing an event of that sort — many of them for the first time. It was less commercial, and more like the Minnesota of his youth; he found himself responding musically to the crowd’s unabashed enthusiasm, singing in a voice that is uniquely his.

After the show, one of the other performers, Tzvi Silberstein, made a comment. “I heard you doing vocals tonight that you never do on stage, or on your albums,” he told Benny. “Why are you limiting yourself?”

The trip back to New York was a long one. “I kept hearing that comment in my mind. I remembered something I’d once heard, an interview with the author of a secular bestselling book. ‘It’s scary to think my best work is behind me,’ she said.

“A long time ago I took one of my songs to my voice teacher in California, Seth Riggs, and asked him to help me sing it,” Benny recalls. “I started singing it for him, and he got very upset at me. ‘You shouldn’t sing this song,’ he told me. ‘It’s not for you! You could start singing this song, I could go out, have a coffee, come back, and you’ll still be doing the same thing!’

“Seth explained it. ‘This is a ‘guitar song’, and you have a piano! You have to work with the voice you have.”

“In Memphis,” Benny says, “I worked with the voice I have, the life experience I bring. I felt like the songs were working for me.

“When Tzvi pointed out how different I sounded that night, I remembered a story. About 12 years ago, I was in Los Angeles for Shabbos and they were mechabed me to daven Mussaf in my yeshivah. I davened a typical chassidish nusach, and after davening, my rosh yeshivah, Rav Schochet, asked me, ‘What was that?’ I told him that I had davened according to the nusach of a chassidishe yeshivah, as a sign of respect. He looked at me and said, ‘For nusach, we don’t need you.’

“At the time, I didn’t get what he was saying, but now I think I do. If you’re going to reach people, you have to figure out what it is you do, what you have to share, and that’s what you should share.

“So I came home davening for a path forward, a way to let myself sing the way I’d sung that night in Memphis.”

He took a deep breath and jumped in.

The sound that came forth was new, but very familiar.

Benny is an out-of-towner. Today, he lives in Crown Heights — as do his parents and in-laws — but he grew up in St. Paul, where his parents raised 14 children while running a famed outreach operation and kiruv seminary. The slick, savvy, self-aware cadences of the New York music scene were far removed from his childhood experience. When other contemporary singers were starring in choirs and appearing on stage, he was wearing a plaid yarmulke and singing classics from Avraham Fried, MBD, and Yom Tov Ehrlich with his siblings around a Shabbos table filled with curious university students. When other singers were using their newfound teenage voices to sing at friends’ weddings, he was leading the niggunim at a backyard picnic at the Lubavitcher Yeshiva in Postville, Iowa. Crown Heights has its share of strange accents, but Benny stands alone there too, fusing Minnesota long, round-mouthed o’s and flat a’s with contemporary New York.

In Lubavitch, there is no such thing as an out-of-towner, but in the music industry, he had to work harder to break in. “It became about doing it right,” he remembers those early years. “Not so much where my voice was taking me, but what worked. I trusted the people around me, they told me it was fine, and I listened.

“Now,” the singer looks genuinely distressed, “I listen to some of that older stuff and I get sad. It seems sort of dull. “

In Memphis, he was playing with his voice, not worrying about doing it right — not worrying at all, in fact, but just singing the way he wanted to. Could he really bring that old-new sound back to New York, back to the recording studio and the slick concert stages where everyone had already pegged what a Benny Friedman song would be?

As he strived to recapture that open, uncalculated vibe, to break open the expectations and rediscover the Benny Friedman brand, he relied on a few allies. “Tzvi Silberstein and Doni Gross got me to stop being afraid. They taught me that if the song sounds a certain way in my head, I could do that out loud too: It added power, it added character, it stopped being one-dimensional. They gave me time and space and most of all, they gave me confidence.”

With their support, he stepped into the studio and began recording a new album, with undertones of that Memphis performance a subtle layer in the music. “I’m not sure people realize what it takes to produce an album. It’s an investment of around one hundred thousand dollars — serious money. You have to really believe in what you’re doing. With this project, I felt a certain freedom and joy, I entered a new zone. In Doni’s studio, I felt like I was going somewhere that was true to me, back to Memphis to sing the way that felt natural.”

He anticipated the criticism. “Moving forward always means moving away from the past, so that didn’t scare me. I’m not locked in place — people change. It’s true for everyone. But I didn’t turn my back on the past; I just used it as a backdrop and springboard.”

The new album, Kulanu Nelech, is Benny — just a bit different than you’ve heard him before.

We listen, his phone on the couch between us: As the first song starts to play, his eyes are open and honest and in them, I can almost see the frozen Minnesota landscape of his youth.

“Kharosho, kharosho slava bogu kharosho, Life is good, life is fine….”

“My father was the Chabad shaliach to St.Paul, a city with many Russian immigrants. One Shabbos, an elderly Russian gentleman comes into shul, it was his first time in a shul since he’d been a child. He received an aliyah, but right after it, he hurried outside. He couldn’t stay in the shul, he was too emotional. By the kiddush, he sits down to eat something and suddenly bursts out, ‘I should have married a Yid and had Yiddishe kinderlach….’ He jumped up and went to kiss the sefer Torah, crying such piteous tears, wailing like a child. It was the saddest thing I ever saw. This old Jew, having faced such nisyonos and hardships, was confronted with the stark truth, and he had nowhere to escape from his pain.”

Benny is still seeing a scene far away from my couch. “He was one, but there were so many others, fighters who would come in with wrinkled faces and worn hands, with such spirit, such fire. They were the most courageous people in the world.”

Benny knew that he was doing a Russian song on this album. “Because if I was being true to who I am, those Russian Yidden of my youth are right there, in every song I sing, their accent, their rhythm, their passion. They knew so little, but their neshamos were so bright.”

The mild drama of the move from slower, traditional, pesukim-based songs so how can we define the change a little better? $$to more universal, Hebrew, faster tunes, comes through in the middle of a song about loving others, a hodgepodge of Hebrew and English lyrics. Suddenly, the tempo slows and Benny is singing slowly, soulfully, the Alter Rebbe’s niggun for “Kol Dodi Dofek.”

“This is what I want to do. Honor where I come from, the music that shaped me, and still sing my song.”

Avromi Werner of KMR Hospitality maintains that there is no singer who can do justice to “oldies” like Benny. “It was after a concert at one of our summertime events,” Avromi recalls, “and we were trying to analyze what Benny’s chiddush is. We concluded that many of today’s singers know the oldies, they might be familiar with the tunes, but they didn’t grow up living them, feeling them in their bones. His geshmak comes from the fact that those niggunim are part of him, he’s singing from within.”

I share the comment with Benny, who appreciates it.

“Yes, the ta’am and flavor of the music we grew up with is very real, but I feel like it can be fused into this, a new sound.”

Concerts, he concedes, are more his setting than weddings — though both are necessary for parnassah. The new album reflects that comfort zone. “This album isn’t aiming to give you catchy first-dance songs — b’ezras Hashem, we’ll do that too — but to communicate a message and vision.”

He searches for something on his phone. “About a year ago, some bochurim released a spoof — a song and accompanying video. The song was a very catchy tune set to the words of the pasuk describing simanei tzoras (leprosy):  “Yerakrak, yerok shebeyerukim, adamdam, adom shebe’adumim — the greenest shade of green and the reddest shade of red.” Their point, I think, was to show what our Jewish music has become, how arbitrary words are now considered songs if you put them to a beat, even if there’s no musical message and no connection with the artist or audience. I loved the way they conveyed that, and I thought it about when I made this album. I don’t just want to sell CDs and have popular songs with catchy beats. I wanted to really say something meaningful.”

He smiles and suddenly, he looks very bashful, like that first-time singer of 2009. “Let’s hope.”

The songs on the new album may be performance-friendly, but the singer himself has his own approach to concerts.

“There was a chassid, Rabbi Yitzchak Meir Kagen, and he once emceed a chassidic concert in Minnesota. I still remember the line he said back then: ‘That we’re on stage and you’re in the audience is just a technicality. In truth, we’re all farbrenging together.’

“I feel that way when I perform — that I’m not singing at the audience, but with them.”

It might sound clichéd, but the thing is, like any hardworking journalist, I corroborated it independently. Friends who were guests at KMR retreats sent me videos, and Benny — resplendent in his kapoteh — is on stage, but he’s got the voice of Motzaei Shabbos in your kitchen, warmth, and candles and what chassidim call ga’aguim.

He brightens. “There are super talented singers who nailed the concert thing: The sound system, the audience, the lighting has got to be a certain way and they rise up to the occasion. I get that. But personally, I appreciate the informality of a Motzaei Shabbos, the smell of pasta, and people sitting bouncing eineklach on their knee… it’s not as intense, but it’s geshmak. It’s real.”

Benny isn’t building a brand so much as inviting you to join him as he is. He’s just being Benny, keeping it fun even as he handles the high notes with perfect control, so that you don’t feel like you’re watching a trained opera singer so much as a talented friend.

At a HASC concert several years ago, the producers brought out the ruling class of Jewish music, Mordechai ben David and Avraham Fried, along with the next generation in their respective families, Yeedle Werdyger and Benny Friedman. It was an informal crowning of the heirs apparent.

I’d been speaking with Benny backstage and I saw his reluctance to accept the designation.

When I bring up his resistance on that night, he shrugs. “No one wants Avremel 2.0, he’s a chad bedara, completely one of a kind. There is no other. If I am him cuz I am him and he is me cuz he is me…” his voice trails off and he cracks up and it takes me a moment to realize he’s actually singing a song from Fried’s Yiddish album.

“He’s a legend. He’s my inspiration and a very good uncle, but I’ll never be him and that’s not my aspiration.”

This article — and Benny’s story — isn’t about Avraham Fried.

Now that we’ve gotten that out of the way, he takes on the admiring look of a fan who finds himself in the same elevator with his hero. “When I say Avremel’s a legend, I don’t just mean musically, I mean by what he’s done with his calling.”

Not long after Benny started singing, he joined a group of singers on a visit to the hospital, where they brought chizuk and joy to various patients. When he returned to Crown Heights, he happened to meet his uncle in the street. “You’re already doing hospital visits? You’re too young for that,” Avremel said.

Benny leans forward and “learns up” the conversation, to the singsong of a chassidishe ma’amar. “What did he mean I’m too young? It’s a mitzvah of bikur cholim, what’s too young? As I did more of these visits, I realized what he meant. When a person is exposed to terminally ill patients lo aleinu, and has to reach into a place of strength to encounter the patient on their terms and find words to uplift, it takes work. Real work. And then you come home and your wife says, ‘It’s been a hard day, the baby hasn’t stopped crying.’ Your first thought is, That’s a hard day? Do you have any idea what hard is? Do you know what I just saw? But that’s wrong. Your wife has her right to tell you about her challenging afternoon and be heard, to be understood. That’s what Avremel was telling me, you need a certain maturity to be able to process what you see and still be able to be a normal father and husband.”

Benny stands up suddenly. “You know what I mean by legend? Here’s a story. My uncle was doing a concert in California, and someone asked if he could swing by the hospital and visit a certain patient. Avremel apologized, but there was no time, he had to go straight from the concert to the airport. That night, Avremel is frantically trying to reach this person — the concert ended early and he has an extra half hour. ‘Let’s go, let’s chap arein a hospital visit,’ he tells the guy, ‘we can do it.’

“That’s a legend.”

He sits back down, this little ma’amar complete.

“By the way, the hospital visits show the most beautiful face of the industry and the one that typical audiences don’t get to see. There’s not a lot of purity left in this business, so many singers are living in a world of hashtag look-at-me, you know? These mitzvos, though, aren’t public and aren’t covered and they’re not easy either. May we never know from it.”

SSometimes I think that there are like ten or fifteen Hebrew words that can be used for album titles, and there’s a gemach somewhere where they give them out to artists. But my cute little joke is cut off by Benny’s passion about his new album’s title track name.

“We called it Kulanu Nelech, because we’re all going. Period. I was just in Eretz Yisrael, and I was listening to some rabbi evangelist on the radio and he was screaming about all the Jews who won’t be part of the kibbutz galuyos, the ones who will stay back. And I was in the car screaming right back at him.

“I travel and meet Chabad shluchim all the time. A shaliach recently told me about being in a shivah house, and food was coming in, platters and cakes and spreads — and none of it had a hechsher. The family of the deceased didn’t know much about halachah, they weren’t religious. And one of the visitors is taking a sandwich out of the house to his car and the grandmother calls out, ‘Hey, Joey, you know that we don’t take out food from a shivah house!’

“Now.” Benny is back on his feet. “I’m asking you: that bubbeh, that grandmother who never went to Bais Yaakov and wasn’t zocheh to what our children are zocheh to, who knows very little about Yiddishkeit and all she has are these little memories — she’s not coming with? She’s holding on tight to that little scrap of knowledge, and she’s not invited?”

I get it.

“It’s like ‘No Jew Will Be Left Behind,’ ” I say, and Benny brightens at the reference to the title track of the first album released by the man who I promised I wouldn’t compare him to but listen, listen close, and it’s inevitable.

“Yeah,” he says happily. “That’s the message, exactly.”

(Originally featured in Mishpacha, Issue 785)