"It's important to never ever give up hope," he said.
"There's something we call the rule of 101 — if you have tried 100 times to help the person, it's probably worth trying 101."
Rehab Remedy #101: A Jail Spell?
The latest footage has led some commentators in the United Kingdom to wonder whether a stretch in jail might not be the best option for Winehouse.
If "her family feels that a prison stint is the best way of intervening, then so be it," Wainwright said.
Winehouse's husband, Blake Fielder-Civil, is currently facing criminal charges for allegedly assaulting and attempting to bribe a pub landlord in East London. Her father has repeatedly accused Fielder-Civil of encouraging his daughter's drug addiction.
As for Winehouse, Friday, she showed up at her husband's hearing in London and blew several kisses at him before shouting, "I love you, handsome, gorgeous one."
Winehouse's spokesperson refused to comment on the video footage, but public interest in her apparent descent into addiction has never been higher.
"The truth is we all love a train wreck," Wainwright said. "Maybe part of it is that addiction is the great equalizer — it's a nondiscriminatory disease," he said, adding that "it transcends gender, race and wealth."
But, according to Gordon, what keeps people interested in Winehouse is "a talent that transcends everything."
"People want to see her get better, there is genuine concern for her," Gordon said, adding that the public usually "forgives people with huge talent."
Fabiola Antezana contributed to the reporting of this story.