Rooney Werner is my primary Living Greyhawk character - the one I played in my first Living Greyhawk adventure back in May 2002, and my sole character (barring one game) for the first three and a half years of my involvement in the campaign. When we first started playing, my wife Bronwyn was more involved in the campaign than I was, and it took me most of a year to get interested in the campaign. Once I did start playing more regularly in 2003, Rooney's personality and my performance came together relatively quickly as an urbane, courteous, and talkative man, and he became a member of the Silver Gryphons adventuring party, the group of characters whose players formed the core of our first home group. Choosing Errol Flynn as the picture reference for Rooney helped focus my characterisation and gave players who recognised the picture an out-of-game "hook" for defining Rooney as a character.
Because I played Rooney and no other character for the first three years of my involvement in the campaign, his character background developed in a more incremental and haphazard manner. In addition, as the only character I played extensively before becoming involved in writing for Perrenland, Rooney has the most connections with Perrenland - both through regional scenarios and through metaorganisations. As a result, Rooney lives in the capital city of Schwartzenbruin with two (NPC) friends, Erich Trumann and Anna Eissfeldt, whose picture references are two of Errol Flynn's co-stars; he's a member of the Voice of the Old Kerk, the bardic college of the Flan pantheon; he's also a rechter, or judge, of Perrenland; he's famous in Perrenland for performing at Das Grunfest, for willing the Schwartzenbruin to Traft yatch race, for being knighted by the Voormann - for being, in short, "that Rooney".
Mechanically, Rooney is also more influenced by in-game experiences than my other Living Greyhawk characters. Unlike my later characters, Rooney wasn't thought out in advance - when I first designed him, it was because we had a session free at the convention and we could play Living Greyhawk if we wanted. In-game events, such as gaining an inherent bonus to Constitution through an adventure, changed my thoughts about how Rooney was going to develop. More important, Rooney's two deaths (both from failing saving throws) led me to change his design's focus from being a single-classed arcane caster to being a high-saves character. That transition led to Rooney taking paladin levels, which in turn led to changes in his characterisation, as he became braver and more valiant, decided to become a rechter, and so on.