Thirteen people made the jump from a 10-metre platform into the Yarra River on the 50th anniversary of the Moomba Festival's hallmark event on Sunday.
Comedian and broadcaster Sammy J, moonlighting as one of the Moomba monarchs who head the festival, didn't exactly lead by example in his attempt to fly through the Melbourne air.
His contraption - a replica of Melbourne's historic Flinders St station with added wings - did little more than pad his landing into the water.
Sammy Evans, representing the Girl Guides Victoria team, summed up the attitude required to attempt the feat.
"You just don't think about it ... and jump," she said moments before an extraordinary flop.
Large crowds lined the Yarra to watch the festivities on the fourth day of the Moomba Festival that marks Victoria's Labor Day long weekend.
Scott Pollard, who has been competing in the Birdman event since 2004, provided one of the biggest laughs when his flying elephant costume landed on top of him after he made the plunge.
Competitors raised money for their nominated causes, with the winner of the longest flight netting $3500 for their chosen charity.
That went to debutant Jack Greenland from Parkes Christian School, whose "quirky biplane-style wing" flew a reported 10m.
Other Moomba events on Sunday included finals of the Australian Skateboarding League round, while some of the world's best water skiers took to the river.
The annual long-weekend event also features a parade with floats, large-scale puppets and 1800 performers on the Labour Day public holiday.