[1] In his early years, Shwekey lived in the Bayit VeGan neighborhood of Jerusalem,[2] but he eventually moved to Polanco, Mexico City, and attended Yeshiva Ateret Yosef.

[3][better source needed] In his young adult years, Shwekey studied in Rabbi Menachem Davidowitz's yeshiva (TIUNY) in Rochester, NY.

[4][better source needed] After studying for a few years in the Deal kollel and his subsequent marriage,[5] Shwekey launched his professional career as a singer.

"[citation needed] In 2008/2009 Vehi She'omdah, composed by Yonatan Razel and debuted on his Live in Caesaria concert DVD, and later rerecorded on Ad Bli Dai, became a major hit.

His latest hits are: Cry No More, Ra'u Banim, Bo'ee Be'shalom, Lo Ya'avod, Am Yisrael, and Et Rekod, among others.

[8] In August 2007, Shwekey and Avraham Fried were slated to headline a major concert in Jerusalem at Teddy Stadium.

[9] Shwekey issued a response that he had already posed the question to Rabbi Ovadia Yosef when an earlier concert featuring him, along with Mordechai Ben David, was also banned.

[11] Yaakov Shwekey headlined a concert together with Shlomi Shabbat at Live Park in Rishon LeZion, Israel and Nokia Arena in Tel Aviv.

[12] On February 25, 2020, Yaakov Shwekey and Kobi Peretz headlined a concert together at the Pais Arena in Jerusalem.

[17] In an interview with Yated Ne'eman, Shwekey said, "I'm convinced that the success I've experienced in my music career is all because of our work with these special children.

"[18] Shwekey had a close relationship with Rabbi Ovadia Yosef, and his single Maran Sheli is dedicated to his memory.

[19][22] Album's arrangers are: Tamir Zur, Ian Freitor, Daniel Kapler, Ravid Kashti, Abie Rotenberg, Moshe Laufer, Avrumi Berko, Moshik Tzabbari and Rafi Greidi.