Jacobson began his career on the stage at the age of 10 with amateur theatre and the Melbourne
Gang Show. At 18, he began his comedy career with regular theatre restaurant, musical theatre, stand-up and MC gigs. He was also hired to play to corporate functions, impersonating business icons and luminaries. 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. Around this time, he had a bit part in the indie sci-fi film
Narcosys alongside future
National Workers Alliance founder Matt Trihey. In 2006, Jacobson starred in the Australian mockumentary film
Kenny as Kenny Smyth, a Melbourne plumber who works for plumbing company Splashdown. The film was a critical and financial success, and is considered to be Jacobson's break-out role. In 2008, he reprised the role for
Channel Ten's short-lived TV series ''
Kenny's World''. In 2007, Jacobson filmed two Australian feature films
Cactus, directed by Jasmine Yuen-Carrucan and released in cinemas in May, and
Newcastle, directed by Dan Castle and released later in 2008. In April 2008, he began his role of Nicely-Nicely Johnson in the major stage production
Guys and Dolls. For this role, he won a
2008 Helpmann Award for "Best Supporting Actor in a Musical". On 24 April 2009, Jacobson guest co-hosted Australian television program
The Morning Show with
Kylie Gillies, while the program's regular male co-host
Larry Emdur was on holidays. 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. It had the best opening weekend for any Australian film in 2009 when it was released on Father's Day. The film was shot on location and features many small towns in country Australia. Jacobson was co-host of the short lived car show
Top Gear Australia with
Steve Pizzati and
Ewen Page which ran for two seasons from 28 September 2010 on
Nine Network to 13 September 2011. In June 2011, the
Herald Sun revealed that Jacobson would be starring in the TV mini series
Beaconsfield, the story of the
Beaconsfield Mine collapse, playing the role of Brant Webb. It aired on Sunday 22 April 2012. In 2013, Jacobson co-hosted the
first season of
The Great Australian Bake Off an Australian
reality television baking competition. Jacobson also starred as Luce Tivolli in the 2013 ABC drama
The Time of Our Lives, which ran for two seasons (2013/2014). In 2018, Jacobson joined the voice cast of
Thomas & Friends, voicing an Australian steam engine called Shane. In mid-2018 Jacobson hosted
Little Big Shots Australia for
Channel 7. In 2019, Jacobson became a judge on ''
Australia's Got Talent'' alongside
Lucy Durack,
Nicole Scherzinger and
Manu Feildel. In June 2022, Jacobson was announced to be returning as a judge on ''Australia's Got Talent'', alongside new judges
Kate Ritchie,
Alesha Dixon and
David Walliams. In 2020, Jacobson starred in the Australian comedy-drama film
Never Too Late which had been filmed in
Adelaide, South Australia the previous year. In 2021, Jacobson was the narrator for the SBS documentary
Inside Central Station. In 2022 he produced and performed in a celebrity tribute to Australian comedian and actor Paul Hogan,
Roast of Paul Hogan, which was broadcast on Australia’s Seven Network. In 2025, Jacobson became a co-owner of a regional Victorian hotel in
Dederang, which was reported to be the subject of a planned reality television series documenting the purchase and refurbishment of the venue. ==Scouting==