He has spent more than 80 years getting up to no good with his pals Wee Eck, Fat Boab and Soapy Soatar and avoid the long arm of arch-nemesis PC Murdoch.
But now a new musical incarnation of Oor Wullie is set to bring the comic strip character up to date by tackling issues of racial diversity and female empowerment.
The star and creators of the show have revealed that the much-loved scamp and his pals will be learning new lessons about "accepting difference" and "what it means to be Scottish" in 2019.
Andrew Panton, the director of Our Wullie, which is staged by Dundee Rep's ensemble theatre company over the festive season before a major Scottish tour next year, said it would it explore the changes in Scotland over the last 80 years as well as key themes about "where we come from from" and "having a sense of belonging.
Martin Quinn, the Paisley-born actor who will play Wullie, said the show would explore whether Scottish people are really as accepting and welcoming as they say they are.
An Indian-born Scottish-actor, Eklovey Kashyap, has been cast as the brand-new character of Wahid, who will help Wullie recover his stolen bucket from school bully Basher MacKenzie (played by Leanne Traynor), who has been "reimagined" as a female character from the famous comic books.
One of Dundee Rep's leading female actors, Ann Louise Ross, will be stepping into PC Murdoch's shoes, while Leah Byrne will have prominent role as Wullie's comic strip love interest Primrose Patterson.
Panton has joined forces with Scottish composers and songwriters Scott Gilmour and Claire McKenzie to create the Oor Wullie musical, which will be unveiled this Saturday at Dundee Rep, 12 years after Sunshine on Leith, a stage musical based on the songs of The Proclaimers, was launched at the same venue.
Panton said: "As with a lot of things that have been around for a long time, Our Wullie has been very male-orientated.
"We’re in a different time now and have different thoughts about representation on stage.
"For many people in our audience it will be the only thing they see for 12 months and for some it might be the first thing they’ve ever seen in a theatre.
"It’s really important that they can see themselves on stage. That’s something we’re always keen to do, but particularly at this time of year when we’ve got a much broader audience.
“It’s a real action-packed adventure and is a lot of fun, but it’s also got a lot of heart. There’s some real thoughtfulness about what home and where we come from really means, about having a sense of belonging and being part of a community, and about what it means to be Scottish.
“These are ever-changing subjective phrases which we need to interrogate frequently. Scotland is a very different country than when Oor Wullie was first around. We're taking a boy on a journey who has witnessed eight decades in Scotland."
Paisley-born Quinn, 24, will return to Dundee Rep, where he starred in his first acting role in the lead role of Oskar in vampire drama Let The Right One In six years ago.
He said: "I think the messages of the show will be clear regardless of whether people are familiar with the books or not.
“To me it is about accepting difference and people coming together. There are messages about being accepting of everybody in Scotland and be as inclusive as we possibly can be.
“There are some great scenes about how, for all say how great it is to be Scottish and that we are so welcoming and accepting in Scotland, we are not maybe quite as accepting as we think we are.”
Gilmour, writer and lyricist on the show with composer McKenzie, said: "Oor Wullie has transcended simply being a comic strip to become a representative of Scotland.
"When you go throw the annuals the things that occur the most are big Scottish themes of family, friendship and the coming together of a community. That’s the stuff that all great stories are made of. When we started to get into that it lessened our fears a bit. It speaks to the very heart of the comic but also speaks to where Scotland is at today."
Panton said he hoped that the on-stage incarnation of Oor Wullie would be true to the comic strip character "that people know and love."
He added: "It’s a brilliant challenge and also a massive responsibility. No-one has ever heard what Oor Wullie actually speaks like and no-one is aware of the physical world or musical world of Oor Wullie. A lot of the challenges have been about how to realise Auchenshoogle and all the characters on stage.
"He’s mischievous, he’s prone to getting into scrapes, he’s lovable and his gang absolutely adore him and are completely faithful to him, even though he doesn’t always have the best ideas. He gets them into certain problems but he gets them out of them. He’s a very loyal friend."
Quinn added: "Wullie sees himself as the leader of his gang but he wants wants to look out for them all. He is caring in that sense.
"Wullie is mischievous, he suffers from a lack of concentration and he also throws himself into things.
"He thinks he is the smartest, the strongest and the fastest. But as soon as he loses his bucket he panics and doesn’t know what to do with himself."
The new stage show will tackle more than 80 years of evolution of popular Scottish culture, with nods to Scotland's traditions of music hall and variety, traditional folk music, and anthems from the likes of The Proclaimers, Runrig and The Bay City Rollers inspiring the score.
Panton said: "Music theatre is so such a big part of Scotland’s heritage. Most Scottish shows that have been successful have got songs in there somewhere.
"One of the early ideas we had was about charting musical styles through the eight decade of Oor Wullie. If you look at the strip it has really morphed and changed in terms of its style and how much it draws on the popular references around it."
McKenzie said: "Since we’re trying to celebrate 80 years of Oor Wullie we really wanted to think about what Scotland would have sounded like back them and what it sounds like now.
"There are so many big, colourful characters in the show which has allowed us to use different musical styles as well - there’s a lot of variety in it. It will definitely celebrate 80 years of Scotland as well as the comic strip."
Quinn said he hoped the show would provide the Dundee audiences with a "release" and some "escapism" from the General Election campaign.
He added: " It is amazing that everybody is now talking about politics as it used to be so boring, but at the same time it just does your head in. You can’t switch your phone on without seeing something about it. Hopefully the show will give people a bit of release from politics over the festive period and take everyone’s minds off it."
Quinn, who has been acting from the age of six, admitted it was a "daunting" prospect taking on such an iconic role, particularly as he does not have a musical theatre background, having studied acting at Guildhall in London after going on tour with the NTS production of Let The Right One In.
He added: "I did do some musical theatre at Guildhall, so I was up for the challenge. I also sing in a band I formed with a couple of pals from drama school. But musical theatre is a big step up.
"We're doing a couple of shows a day over the festive period so I just hope my voice holds out."
Panton said: "When I first started talking about doing Oor Wullie here and got the show into development the actor I really had in mind was Martin.
"That sets yourself up for a problem if they are doing something else, but fortunately for us he was available and did an amazing audition for the whole creative team. We all knew he was the person to play Oor Wullie.
"He is a fantastic actor, his sense of comedy and storytelling is second to name, and is a great singer. We’ve got a top-notch cast and I’m really looking forward to seeing how they resonate with our audiences."
Oor Wullie is at Dundee Rep from 23 November-5 January and will then tour to Glasgow, Edinburgh, Ayr, Inverness, Stirling, Aberdeen, Kirkcaldy and Greenock next year.