I don't know the timeline of his uphills and downhills. I remember hearing about it a while back, a quick google shows as early as mid-2009.
Seems like he was played in bands in the mid 90s as a teen, was mekarev by Chabad in 98, studied in Morristown/Tiferes and Hadar Hatorah in Crown Heights (Chabad BT yeshivas) in the late 90s/early 00s, did small concerts and made it onto CNN by 2003,
Released Shake off the dust, got married, and got his first late night interview in 2004 with Kimmel where he says he wouldn't play on shabbos for 1, 2, or even 4 million dollars:
Youth came out in 2006 which was the peak of his record sales and popularity, No place to be came out in 2007 and then his roots tonic band disbanded.
Late 2007 he meats his guru in Jerusalem, drifts away from Chabad and into Karlin and other sects. Takes off the beard in 2011 but claims to still be religious, in 2012 releases Spark Seeker and appeared in public without a yarmulka for the first time since becoming religious, divorces in 2013, and released akeda and schedules his first concerts on shabbos and YT in 2014.