Early in his career, Ryan was involved part-time in pirate radio – presenting a selection of programmes firstly for Alternative Radio Dublin (ARD) and then for Big D.
Ryan presented RTÉ 2fm's only show which was regularly among the top twenty Irish radio shows in Ireland, a show which commanded around €4–5 million for RTÉ per annum, mainly through advertising (one thirty-second advertisement during the show cost €900).
For the first time it occurred to Ryan that the story was more important than the question.
In October 1990, Ryan received a Jacob's Award for The Gerry Ryan Show, described at the award ceremony as "unbelievably bizarre and unprecedented – and at the same time being serious, hilarious and unpredictable".
Producer Kevin Linehan, was removed from the show to work on the Millstreet Eurovision and asked Ryan to co-present the event with Fionnuala Sweeney.
Ryan then moved to a night-time music show called 'Lights out' which accompanied Mark Cagney's grown-up album programme and Dave Fanning's The Rock Show as part of Radio 2's night-time line-up.
The trio brought their shows on tour around Ireland.
He soon began a relationship with the former South African Ambassador to Ireland and the then UNICEF Ireland executive director, Melanie Verwoerd.
Ryan was found dead in his Dublin flat on 30 April 2010. He described his father, Vinnie, as a "slightly eccentric" dentist from a Presbyterian background and his mother, Maureen, as "a flamboyant woman" who came from a theatrical background and worked in the theatre.
Each morning he would begin by discussing the headlines of that morning's newspapers.
Following the news update at , Ryan would introduce that morning's Nob Nation, a satirical slot which featured impersonations of politicians and RTÉ media personnel comparable to rival station Today FM's Gift Grub.
They were good friends; Fanning was "a kind of hyperactive, Southside rock guru" and Cagney was "this obsessive, meticulous Corkman who would annotate every single millisecond of what he played on-air".