20 years of Ross O’Carroll-Kelly: Paul Howard’s top 20 moments

‘Reading the first column now, at a remove of almost 20 years, the big surprise is that there was ever a second one’

1. Where Ross Doesn’t Drink Heineken (1998)

It all started in the autumn of 1997. I was in the Sunday Tribune newsroom one Friday evening talking to Hugh Mohan, the newspaper's barrister. We were exchanging funny stories about schools rugby players behaving badly. I'd recently been stopped from getting onto the Dart by a boy in a blazer, who placed a staying hand on my chest and said, "Sorry, dude, this is a Rock carriage!" I told Hugh I wanted to write a fly-on-the-wall, documentary piece that detailed everything that went on behind the scenes in that gilded demimonde, then we both laughed at the idea that a newspaper could write about the teenage sons and daughters of Ireland's middle classes in such a way.

Ross O'Carroll-Kelly was born out of that conversation. The first column appeared a couple of months later in the first week of January 1998. Fictional journals were in vogue at the time and I was inspired by two in particular: Jim White's Darren Tackle column in the Guardian but most of all Helen Fielding's Bridget Jones's Diary. The name, with the initials that spelled out RO'CK, was the invention of the newspaper's deputy editor, Ger Siggins.

Reading the first column now, at a remove of almost 20 years, the big surprise is that there was ever a second one. My toes curl when I read the first line: “The schools cup is only, loike, two weeks away, royt, and my mind is, loike, toadally fried, man…”

It took me a year or two to find an authentic voice for the Ross O'Carroll-Kelly character. The early columns, which appeared in the sports section of the Sunday Tribune between January and March 1998, were preliminary sketches that I might have worked harder on if I'd imagined that it was going to last more than a few weeks. Instead, the column was wound up after Ross missed the deciding kick in the 1998 Leinster Schools Senior Cup final.

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I used fictional names for everything, which also makes me cringe. Blackrock College was Blackstones College, Mount Anville was Anville Hill, Kielys was the Horse and Trap and Annabel's was Jezzebel's. Ross's friends weren't Oisinn, Christian and JP; they were named Terry, Newer and Gicker. It was very low on subtlety.

No one had a mobile phone. Ross drank Miller rather than Heineken, dreamed of driving his own 1.6 litre Peugeot 205 (seriously?) and had a kid brother called Jamie (yes, JO'CK!) who brought the half-time oranges on to the pitch and raised his middle finger to the opposition crowd. I don't know what happened to Jamie. When I revived the column in December 1998, with Ross repeating his Senior Cup year, I forgot that I'd ever given him a brother.

2. Where Fr Fehily Sings ‘Castlerock Uber Alles’ (1999)

My colleague Dave Hannigan used to complain that the only priests represented in modern Irish fiction were bad priests. I decided to make Fr Denis Fehily a good priest, albeit one with an unhealthy obsession with the iconography of 1930s fascism. When I covered schools rugby as a freelance sport reporter, it always fascinated me how many of the anthems of the so-called elite schools had a slight Hitlerian flavour. Fr Fehily's first scene was when he led a school assembly in the singing of Castlerock Uber Alles, a song that talked of "shying from battle never" and marching on the Sudetenland. Fr Fehily was my Boba Fett – I killed him off way too soon.

3. Where Ross Lifts the Leinster Schools Senior Cup (1999)

Except he didn't. In the original column, it was his friend, Simon, who captained Castlerock College to victory against St Muckers in March 1999 and, before lifting the cup heavenwards, shouted, "For Mom! For Dad! For Rock! For God!" A colleague had told me about a former Blackrock captain who once used this exact toast although I never found out if the story was apocryphal. When I turned the early columns into the first Ross book, The Miseducation of Ross O'Carroll-Kelly, I made Ross the captain and put the words in his mouth instead. As the St Muckers (later, Newbridge College) players came down the steps with their runners-up medals, Ross says, "Loser!" to each one, which reminds me that in the early days I was trying to make the character as hateful as possible.

4. Where Ross Goes to Two Debs Balls on the Same Night (2000)

An early test of Ross's skill in handling the deadlier of the species was when he took on the challenge of taking two girls to two different debs balls on the same night. The Holy Child Killiney bash was on in Jury's Hotel of Ballsbridge at the same time as the Loreto Foxrock event around the corner in the Berkeley Court. Ross spent the night running between two chicken supreme dinners and two unsuspecting dates. It was one of the first times I used the names of real schools, which grounded the series in reality.

5. Where Oisinn Wins the Iron Stomach Contest in UCD (2000)

This wasn't fiction as much as it was journalism. When Ross won a rugby scholarship to UCD, I used to go to Belfield once a week for storyline ideas. I was there to see the Freshers Week Iron Stomach Contest, in which a line of students wolfed down toothpaste and cat food sandwiches and Weetabix slathered with ketchup. The last one to vomit was declared the winner. In those days, I still hadn't put my name to the column, so no one knew what I looked like, just that there was a mole in their midst. One student rang the sports desk and said: "I know who's doing that column – it's either Scalls or Drico." Scalls was Ciaran Scally, the former Blackrock captain, who was part of the UCD Rugby Academy. And Drico? Yes, it was He!

6. Where Ross Goes to Tallaght to Reclaim his Mobile (2001)

I'm often asked to read this one at public events but it's really just a punchline. Ross had his mobile phone – one of those early Nokia house bricks – stolen and his friend, JP, drove him to Tallaght to retrieve it. Ross nodded off in the car, then got a fright when he woke up and looked out the window. "The horror!" he said. "The depravity! How can people live like this?" To which the response was: "Ross, we're still in Terenure. "

7. Where Charles Fails to Finish the Women’s Mini Marathon (2003)

In the early days, Ross’s father – who didn’t yet have a name – was a serious, authoritarian figure who had little time for his son. As time went on, I realised that the column was too heavy with chip-on-the-shoulder, class-related satire and light on likable characters in amusing situations. I remembered once hearing a schools rugby player tell his father: “I don’t give a fock how you think I played – just crack open the wallet.” I stole that father-son dynamic and Charles softened into the lovably corrupt blowhard who ran the Women’s Mini Marathon as a protest against women being granted full-membership of golf clubs.

8. Where Fionnuala Pickets Funderland (2003)

My first job in journalism was with Southside in the late 1980s, when I met a lot of posh ladies protesting against various things – very often halting sites – that they considered "inappropriate" for their area. Ross's old dear was based on one of those perennially "up-in-orms" types and her Move Funderland to the Northside campaign was the most south Dublin protest I could imagine. It was around that time, in the early 2000s, that the column stopped being a send-up of rugby culture and became more of a send-up of the Celtic Tiger.

9. Where Hennessy Coghlan-O’Hara is Forced to Flee the Country (2004)

I thought Charles should have a lawyer sidekick like Oscar Acosta in Hunter S Thompson's Fear and Loathing in Las Vegas. The name was an in-joke between me and my friend Róisín Ingle when she worked in a job where she wasn't allowed to take personal calls. I used to tell the receptionist my name was Hennessy Cognac-O'Hara from Hennessy Cognac-O'Hara and Associates. When the corrupt-to-the-bone Hennessy asked Ross to drive him to Dublin Airport in the boot of his car, Ross took the scenic route via Avondale Road in Killiney, known locally as the Road of a Thousand Speed Ramps.

10. Where Ross Discovers he’s the Father of a Seven-Year-Old Son (2005)

A friend who went to a Jesuit school once told me about a well-meaning, cross-city, student exchange programme he took part in called The Urban Plunge. He remembered spending two weeks in Finglas trying to get off with the older sister of the student he exchanged with. I thought "Hey, what if…?" and seven-year-old Ronan entered Ross's life in 2005. I imagine him as a mix between Dustin the Turkey and a kid I knew who was impossibly tough and streetwise for his years. Ronan allowed me to reveal a softer, more sympathetic Ross, which was good because, despite my earlier misgivings, I was beginning to grow rather fond of him.

11. Where Ross Saves a Seal from an Ecological Disaster (2005)

Well, kind of. Ross’s marriage to Sorcha failed. In fact, it failed to last beyond the soup course at the wedding. He needed a big gesture to win her back, so he “borrowed” an anaesthetised seal from the veterinary practice of one of his occasional girlfriends, drove the animal to Killiney Beach, smothered it in black “guck”, then phoned Sorcha and told her to come quickly with her father’s garden hose and a bottle of washing-up liquid. They rescued the seal – and their marriage.

12. Where Honor is Born (2005)

Sorcha went into labour at a book launch in the ballroom of the Conrad Hotel and her grandmother delivered Honor into the world a short time later. While Sorcha recuperated in Mount Carmel, Ross enjoyed a quiet moment with his new daughter, looking out the window, across the golf course, and telling her about all the fun they were going to have together. Like many south Dublin fathers, he had no idea of the world of trouble he had just entered.

13. Where Charles is Sent to Prison (2007)

Ross O'Carroll-Kelly appeared in The Irish Times for the first time in September 2007. In the first column, Charles was sentenced to five years in Mountjoy for tax evasion and planning corruption, forcing Ross to stand on his own two feet, with a wife, two children and a recession on the way.

14. Where Ross Pulls a Girl on Wheels (2008)

Ross chatted up an American girl named Shauna in Eddie Rockets on South Anne Street but then tried to lose her when he discovered that she was wearing rollerblades. Before he managed to shake her, Shauna got the wheels of one of her skates caught in the Luas line at Stephen's Green. With Shauna standing on one leg, and a large crowd following, Ross was forced to push her to the top of Harcourt Street, where the track went overground, allowing the skate to slot out.

15. Where Sorcha is Forced to Close Her Fashion Boutique (2009)

I was toying with the idea of ending the Ross O'Carroll-Kelly series in the summer of 2008. I'd done everything I wanted to do with the character and was keen to return to sports writing. Then the recession struck and it was a new challenge to write about Ross, his family and his friends in this changed world, where all the certainties that underpinned their lives were washed away. Reading back through much of what I wrote before 2008 is like performing an architectural dig on Ireland's economic past. So many shops, restaurants and nightclubs namechecked in the early Ross books disappeared overnight, including Renards, Pia Bang Home – and Sorcha's clothes shop in the Powerscourt Townhouse Centre, which became a euro store. The next three books I wrote – The Oh My God Delusion, Nama Mia and Downturn Abbey – were a kind of recession trilogy that explored the efforts of Ross and his privileged peers to adjust to an apocalyptic, post-Tiger world.

16. Ross is Forced to Dress as the Dowager Countess of Grantham (2013)

I wrote this piece as a paean to Bray, a town I happen to love but one Ross despises with all of his heart. Ross was forced to dress up as Maggie Smith's Violet Crawley for a Downton Abbey theme party in a house in Ardmore Park. On the way home, on Bray Main Street, the car ran out of fuel and he was forced to walk several miles to a petrol station while wearing a long skirt, mid-heeled pointed brogues, a pillbox hat and a full face of make-up.

17. Where Honor Infests her School with Rats (2014)

Like most parents, I expect, Ross and Sorcha dreamt that their daughter would come to reflect their best qualities back at them. But I had no interest in writing about such a child. I wanted Honor to have her parents' worst qualities – her father's obnoxiousness and her mother's princess complex. In Keeping up with the Kalashnikovs, she secretly bred an army of rats and let them loose in Mount Anville during the Christmas concert. It set a high bar for brattish behaviour that I realise I have to raise with every book. Honor is the character I'm asked about most often. Mums and dads seem to especially like her, presumably because she makes their own children seem like angels by comparison. She was inspired by a little girl I saw at Dublin Zoo who was trying to capture an image of a majestic, prowling tiger on her iPhone, except the animal kept moving out of the frame a split-second after she took the picture. After nine or 10 frustrated attempts, she finally got the shot she wanted, then shouted at the tiger: "At! Focking! Last!"

18. Denis O’Brien Sues Charles for Having Denis O’Brien Hair (2016)

Charles found a wig in the attic, put it on his head and discovered that the entire country was suddenly, mysteriously, bending to his will. But then Denis O’Brien sued him, claiming that his new, perfectly globular hairstyle was a breach of his own intellectual property rights. The real Denis O’Brien didn’t send me so much as a cease and desist letter. In fact, I ran into one of his friends in a restaurant recently, who assured me that Denis found the whole thing funny, which in satirical terms probably made the storyline a big, fat fail.

19. Ross Helps Seapoint Avoid Relegation from Division 2B of the All Ireland League (2016)

At the very outset, I thought that Ross was going to become a hugely successful rugby player – treading much the same path that Brian O'Driscoll travelled. But often failure is more interesting to write about than success. Ross was destined to become one of those rugby club bores who could have been the greatest if it wasn't for bad luck and injuries. Then, 16 years after he last played the game, Fr Fehily led him to Seapoint Rugby Club in – let's be honest – Ballybrack, where he earned his rugby redemption, not as a kicker but as a hooker.

20. Ross Doesn’t Understand the Meaning of Pronouns (2017)

The definition of what is politically correct and incorrect is evolving all the time. If you don't stay on top of the updates, you can find yourself accidentally causing offence. Then you've suddenly made millions of enemies on social media, just like Ross does in Operation Trumpsformation, when he meets Broderek, who asks to be referred to using they/them pronouns. But old grammatical habits die hard.

Operation Trumpsformation by Ross O'Carroll-Kelly is published by Penguin Ireland at €15.99. Paul will be signing copies of his book on SAturday, September 23rd at 3pm in Easons, Dundrum Town Centre, Dublin.

CREATE A NEW ROSS CHARACTER

To celebrate 20 years of Ross O’Carroll- Kelly, enter our competition to create and name a character in Ross’s next book.
The prize includes an overnight stay for two in a newly refurbished Heritage room in The Shelbourne Hotel and tickets to a Leinster rugby match, plus, runner-up prizes of the book, Operation Trumpsformation.
For more details see irishtimes.com/ross20