Singing Your Song: An Intimate Conversation With Hit Singer Yaakov Shwekey – COLlive

Ahead of his upcoming concerts in Florida during Chol Hamoed Pesach, hit singer Yaakov Shwekey sat down with COLlive reporter Mendy Wineberg for an exclusive interview. Among other topics, Shwekey discussed his passion for music, his relationship with Akiva, and his plans for the future. The music legend also shared his advice for aspiring singers and some personal moments from his singing career.

Two of Jewish music’s biggest stars, hit singer Yaakov Shwekey and Israeli sensation Akiva, will be performing together in Florida during Chol Hamoed Pesach. An entire production crew is scheduled to arrive from Israel to produce the events, and the concerts promise to offer the highest quality of music and entertainment.

With the excitement growing as we head closer to Pesach, I sat down with Shwekey for an exclusive interview to give readers the inside scoop from the legend himself. His friendly and easy-going personality immediately put me at ease and the conversation flowed seamlessly through a multitude of topics; from his passion for singing to his advice for aspiring singers and his plans for the future. I hope you enjoy it as much as I did!

Mendy: Reb Yaakov, it’s an honor to talk with you today. You have been singing now for over 20 years. How would you describe your role as a Jewish entertainer?

Shwekey: I regard my work as a singer as a calling from Hashem. The Torah emphasizes the importance of being a positive influence and I see that as my goal; to uplift, inspire, and bring joy to others. We all need to use our talents to bring other people closer and my position enables me to connect our fellow Yidden to our heritage through music.

Mendy: That’s a great perspective but after so many years in the business, I would imagine that the inspiration wears off. How do you keep it going?

Shwekey: Learning is the most important component. To inspire others, your message has to come from the soul and that can only be achieved by being connected to learning and the ideas that shape us. Young, aspiring singers often call me for advice and my response is always the same: If you sing from your heart because you feel it and you believe in it, you’ll capture the hearts of your audience.

Mendy: Like the idea of devarim hayotzim min halev, nichnasim el halev – words that come from the heart can penetrate the heart?

Shwekey: Right, but it’s even more so with music. They say music is the pen of the soul and when you sing from your soul it affects other people in amazing ways.

Mendy: Can you share with us a moment during your singing career when you personally witnessed this?

Shwekey: There are so many that stand out. One particular story that really moved me happened when I was davening once at a Shul in Manhattan and a young man approached me and began gesturing toward his tefillin. Seeing my confusion, he explained to me after davening that a concert of mine had been the first Jewish concert he had ever attended and the experience turned his life around to the extent that he was here in Shul many years later wearing tefillin because of it.

Mendy: This is almost starting to feel like a farbrengen but I want to change the subject for a moment to talk about your upcoming performance with Akiva. You’ve performed with him a number of times already now, most notably at HASC last year. Is there something that you feel you have in common with him that makes you both complement each other so well on stage?

Shwekey: To sing with somebody else, you need to have a strong rapport with that person. Akiva and I have a great relationship both on and off stage and I believe that spills over to the audience when we perform. While Akiva’s style is different from mine, I appreciate him as a deep, spiritual person with a real longing to connect to hakadosh baruch hu and I think it comes through in his music.

Mendy: His style is certainly different from yours and the Israeli band that will be playing is probably not what people here in America are used to. Do you feel that it will bring a different energy to your performances?

Shwekey: Israeli artists and their style of music bring a totally different energy and that’s the beauty of it. People love to be surprised and see something unique and different. In fact, Akiva and I sang together at an event for my wife’s organization in Yerushalayim and people wrote to me afterward that from all the concerts they had been to, they had never experienced one quite like that. The fusion of our different styles makes for a very unique and special blend.

Mendy: I couldn’t agree more; watching you perform together is enthralling! You mentioned earlier how important it is for you to uplift your audience by giving them a message through the music. With these concerts happening during Pesach, what is the message that you hope to convey through your songs?

Shwekey: Pesach is all about unity. We bring the family together – והגדת לבנך – to tell the story of Yetzias Mitzrayim and celebrate who we are as a people. For some, that message comes from the spoken word during maggid at the seder. For others, it needs to be conveyed with a hug, through a song, and by experiencing Yiddishkeit with joy. I often hear from people that they came to a concert for entertainment and walked away feeling excited about Yiddishkeit. That’s what it’s all about.

Mendy: We can’t sit here just weeks before Pesach and not discuss your song Vehi Sheamda. It is not an exaggeration to say that it is sung by literally millions of Jews around the world on the seder night. How does that make you feel?

Shwekey: It’s really an indescribable feeling that simply can’t be put into words; I get emotional just thinking about it. As is, the seder night is a powerful time but when the family sits together and recalls such a foundational message with a tune that is so moving it just reaches a different level. When I go somewhere for Pesach and I see everyone with their arms around each other singing this song, I feel so lucky to have been a part of it.

Mendy: But there are so many nice songs out there. What do you think it is about this one that strikes such a cord with people?

Shwekey: Firstly, the tune is really something special. When I first came out with the song, I was told by some of the biggest names in the industry that this was one of the nicest songs they had ever heard. Then there are the words that harken back to our people’s suffering throughout the ages and how hakadosh baruch hu matzilenu – Hashem delivered us from those times to bring us to where we are today. It’s the perfect recipe for a song that will never be forgotten.

Mendy: There is a lot of excitement building around the upcoming concerts. What is something new and exciting that people can look forward to seeing there?

Shwekey: We plan to spice up some songs that have been sung in the past, and also do songs that people haven’t yet heard us sing together. Besides, every Yom Tov brings its own unique energy and there’s nothing like the vibe of Pesach in sunny Florida. It’s going to be incredible!

Mendy: I’m sure it will be. Looking beyond Pesach, what can we hope to see from you later this year?

Shwekey: We have been working really hard on a new, Israeli-style album, one similar to Kolot that was such a hit a few years ago. We are still looking for a few more songs to give it the energy that we want and it will be ready. If all goes well, it’s on track to be released around Sukkos time.

Mendy: I really enjoyed this conversation together today. I’ve learned so much and I’m sure our readers will too. Wishing you much hatzlacha and a kasher un freilichin pesach!

Shwekey: It’s been a pleasure! Wishing you and all your readers a chag kasher vesameach!

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