Where Country and Soul Music Merge

As Country Yossi paints a picture of the development of his persona, he also provides a moving glimpse of the sensitive soul that created some of the frum world’s most beloved country music
Despite his frequent appearances in print, radio, and music albums, there’s a lot that people don’t know about Country Yossi. In a candid conversation, the popular entertainer divulges how a kid from East New York became known as “Country Yossi,” shares his memories of Rav Shlomo Freifeld, describes his original unintended foray into children’s entertainment, and reveals the secret behind the skyrocketing popularity of his radio show (“give away free prizes!”). But as he paints a picture of the development of his persona, he also provides a moving glimpse of the sensitive soul that created some of the frum world’s most beloved country music
There’s a very special man, in a very special place, there is wisdom in his eyes and a smile upon his face. In yeshivah he’s the Rebbi, he’s your Rebbi and your Rebbi is your friend … Someday, when you’re older and much wiser, you’ll realize how much you don’t know. You’ll look and cry up to Shamayim, oh Rebbi, I miss you so …
These were the words that determined that I simply had to meet Country Yossi, or Yossi Toiv. Deeply immersed in the research for my book on the life and impact of Rav Shlomo Freifeld, ztz” l, the lyrics to this song, which was written by Yossi Toiv in honor of Reb Shlomo, made me realize that beneath the exterior of Country Yossi’s legendary humor and hilarity lies a deep, sensitive soul.
Today, the name Country Yossi is associated with his popular radio show and monthly magazine, both of which are comedic in nature. The man himself, however, is far from a comedian. To be sure, the laughs come easy and the quips are plenty, but there is a certain quiet pensiveness about him as well.
The Boy From East New York
Yossi Toiv grew up, as did so many others in that time, in East New York. His grandfather was a distinguished Lubavitcher chassid, and as such, he attended the Lubavitcher yeshivah. He credits the principal there, Rabbi Schrage, with developing his creativity. “I wrote up a few pages of what I thought could be sort of a school paper and showed them to him. He was delighted, and mimeographed several copies for me to sell. Shoin, I was in the magazine business!”
He grew up in a home filled with song. His father, Reb Chaim Toiv, is a chazzan of great renown and a former talmid of Mesivta Rabbeinu Chaim Berlin. Reb Chaim sent his son to the yeshivah — which was then in Far Rockaway — as well. Yossi recalls sitting and chatting with a group of his friends one Friday afternoon, waiting for Minchah to begin, when he got his first glimpse of Reb Shlomo Freifeld. “He walked into the beis medrash, this immense man with peyos dripping wet, a flowing beard, and the widest hat I had ever seen. We had heard rumors about a new menahel, and we gulped at the thought that this might be him. He was huge. But then he smiled and introduced himself and said, ‘Come boys, let’s learn some Mishnayos together.’
For the next twenty minutes, they sat riveted while he taught, and by the time he rose, they were sold. “At the end of the year, Reb Shlomo informed me that he was starting his own yeshivah — Sh’or Yoshuv — and invited me to join. I was thrilled.”
Reb Shlomo had grown up in East New York, just like many of the boys, and he would remind them of that. “He would smile and place his arm on my shoulders, and say ‘I’m just like you!’
Musical Pioneer
Country Yossi was an early pioneer in the Jewish music scene. That, too, has its roots in Sh’or Yoshuv. “I was roommates with Shmelkie Brazil — today Rav Shmuel Brazil, a rosh yeshivah at Sh’or Yoshuv — and he had a guitar,” Yossi remembers. “He would come running into the room sometimes, totally aflame, and start playing. He’d had an inspiring thought or uplifting emotion that he had to commit to music. I remember when he composed his classics: “Bilvavi” and “Shmelkie’s Niggun.”
“Anyhow, when I expressed interest in learning how to play, he drew me up a chord sheet and I would just play around with his guitar. In time, I grew pretty proficient at it.”
When did you start writing songs? I ask.
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