The private backyard wedding was made public by Daniel Zamir, a close friend of Matisyahu, born as Matthew Paul Miller.
"I have traveled to many concerts and many places but it is rarely as exciting as playing at the wedding of a best friend ..." Zamir wrote on Facebook on Monday. "I got to play at Matisyahu's first wedding 16 years ago and today I've come to New York, New York to play again at, God willing, his last wedding! Good luck to the young couple and to all of the people of Israel with them!"
Zamir posted a video of him playing Od Yishama, a tune often sang during Jewish wedding ceremonies, specifically after the new couple descends from the chuppah. Zamir, an Israeli-born saxophonist, has preformed with Matisyahu, and played at his first wedding.
Matisyahu, divorced in 2014, was first married in 2004 to a different woman named Talia. They have two sons, Shalom and Menachem Mendel.
Around the same time as his divorce, Matisyahu shaved off his locks and beard, shocking many of his fans.
"I was affected by all the things people were saying about me - by my own fans and certainly by my own people and the religious community that had seemingly supported me for such a long time," Matisyahu told the JC in an interview in 2014.
Since then the reggae star has developed his image and his tunes. Matisyahu has also received some harsh feedback from many of his fans when he started dating his now wife. In one Instagram post where Matisyahu showed a video of him teaching Dressler to drive, some fans questioned Matisyahu for dating a much younger woman.
Regardless of some fans critiques, many have shown support, with just under 100 likes on Zamir's video only a few hours after the big event.