He was nominated for two South African Music Awards, including best single for "Once in a Lifetime" and best pop album for One Step Closer.

In 2003, with the inaugural World Idol competition, Winckler came fourth behind Belgium's Peter Evrard (3rd), the US's Kelly Clarkson (2nd), and Norway's Kurt Nilsen (Winner).

He performed "Chasing Shadows", the theme song for the South African release of the 2003 Disney movie Treasure Planet.

[1] Albums Singles He performed in the role of Roger Davis in the touring production of the musical Rent from the 2007–2008 season.

In 2015, Winckler starred in the romantic comedy Mooirivier playing a singer performing at an Easter music festival.