In 1999, Jacobson received a regular segment on Melbourne's Gold FM radio station, called The 60 Minute Challenge.

He also created the character voice of Sergio the Hairdresser, who featured regularly on Gold FM's Breakfast Show.

Jacobson's focus eventually moved towards the camera and he began acting in music videos, short films and television commercials whilst continuing to perform audience warm-ups for major TV networks.

In April 2008, he began his role of Nicely-Nicely Johnson in the major stage production Guys and Dolls.

In 2009, Jacobson co-starred with Paul Hogan in Charlie & Boots, an Australian film in which Boots (Jacobson) takes his father, Charlie (Hogan) on a road trip to fish on the northernmost tip of Australia because of something his father told him they would do one day, when he was a kid.

[6] Jacobson also starred as Luce Tivolli in the 2013 ABC drama The Time of Our Lives, which ran for two seasons (2013/2014).

In 2019, Jacobson became a judge on Australia's Got Talent alongside Lucy Durack, Nicole Scherzinger and Manu Feildel.