When Brownless retired from football he moved into the media, appearing regularly on
The Footy Show. On
The Footy Show he appeared in "The House of Bulger" segment as the family's matriarch Joybell Bulger. He joined
95.5 K-Rock in Geelong as a sales representative. Soon, on their "Big Mattress" breakfast show, he co-hosted a sport/comedy segment called "On The Bench" with ex-Geelong player
Dwayne Russell and the Essendon fanatic "Ferret" (Russell Taylor), twice a week. A long list of Geelong players were included in "On The Bench" as special guests including Barry Stoneham, Tim McGrath and Paul Couch. He regularly appears on the station promoting Wombat Gully plant farm Geelong. In 1992 he became the inaugural winner of the
Mirrool Silo Kick in the
Riverina, kicking an Aussie Rules football 32 metres plus over the Mirrool Silos. In August 1999, it was reported that due to Brownless' connections in the local political scene, both the
Australian Labor Party (ALP) and the ruling
Liberal Party of Australia were keen to recruit Brownless into politics, despite his limited experience. Labor leader
Steve Bracks, who would go on to win the state election that year, was a Geelong supporter, and Brownless had persuaded the then Premier
Jeff Kennett's wife, Felicity, to become Geelong's female
number one ticket holder. By 2005, Brownless had featured on
The Sunday Footy Show as well as earning continual appearances on
The Footy Show. He also co-hosted
Morning Glory, a weekday breakfast show on Melbourne radio station
SEN 1116. Brownless finished his 5-day-a-week stint in November 2008. Brownless appeared on
Before the Bounce, a weekly football show on
Foxtel alongside
Jason Dunstall and
Danny Frawley until the end of the 2008 AFL season. In May 2008, Brownless was added as a regular on the Thursday night AFL Footy Show to replace an incapacitated
Sam Newman, but he was relegated to guest panelist upon Newman's return. From 2009 until the show's termination in 2019, Brownless had once again become a regular alongside
Shane Crawford to replace
Trevor Marmalade, alternating each week with Crawford and, since 2012,
Matthew Lloyd. In March 2010, Brownless joined
Triple M Melbourne's new drive show
The Rush Hour with
James Brayshaw. Brownless bought the Cumberland Hotel in
Castlemaine, Victoria. In January 2020, Brownless appeared in the
sixth season of the Australian version of ''
I'm a Celebrity...Get Me Out of Here!''. In September 2021, Brownless announced he was leaving
The Sunday Footy Show and the
Nine Network after 27 years with the network. ==Personal life==