She met the other members of the group, which over time included Tom Gleisner, Rob Sitch, Santo Cilauro, Tony Martin, Mick Molloy, and Judith Lucy amongst others, whilst working on Melbourne commercial radio on the D-Generation Breakfast Show. Kennedy was not originally a member of the group, but was the newsreader assigned to work with them during their timeslot. The team quickly made a game of trying to make her laugh while she read the news.
After their frequent success in this aim led to Kennedy's sacking, the D-Generation adopted her as a member and she continued to work with them on the radio show. The group stayed together to later write, direct and produce The Late Show, a comedy sketch show, and Frontline, a widely acclaimed spoof of television current affairs in which she played ambitious reporter Brooke Vandenberg.
Since the mid-1990s, Kennedy has mostly stayed behind the camera as a producer for various Working Dog productions, including their panel talk show The Panel, and the films The Castle and The Dish. Kennedy also appeared on the radio program Get This occasionally, and has been a semi-regular panellist on television chat show The Circle. In 2009, Kennedy released her first cookbook, Fabulous Food Minus the Boombah. In 2010, she released her second cookbook, OMG! I Can Eat That?.
