A born entertainer, he had been singing for years - all through the 1920s - at informal "back green concerts" held in the Grassmarket.
"There was no amplification then so you had to have a strong voice," he recalls. "The winner got 1 as a prize, which was a small fortune in those days."
But while he was as keen as could be, that moment wasn't the youngster's time to shine - contestants had to be over the age of 14 to enter the talent show and, on this occasion, the police were waiting in the wings, ready to cart a tearful Tommy away from the limelight.
His first brush with fame, however, certainly wasn't his last and the 85-year-old has now been entertaining audiences in the Capital for more than 70 years, first as a performer then as an events organiser, helping many charities in the process.
Now, in recognition of his work, Tommy has been awarded the Sir William Y Darling Bequest for Good Citizenship, which was due to be presented to him last night by Lord Provost George Grubb in a ceremony at the Lothian Chambers.
In fact, Tommy's only break from showbiz was when the Second World War broke out and, at 17, he volunteered for the Army.
"All my friends were a bit older than me so I joined the Army and left the city," he recalls. "I didn't want to be left behind so I volunteered for the Army and joined the Black Watch."
Tommy was stationed in Shetland, where he worked as a driver, and at an aerodrome at Donibristle in Fife, where he witnessed a German plane bombing the Forth Bridge.
"I was proud of being in such a historic Scottish regiment and I was just a young man, so I never thought about being scared or nervous," he recalls. "When you live through something like that, you think nothing of it. It's only when you are reminded of it later on you see how big it was."
It was when he was stationed in Yorkshire - with the Royal Army Service Corps - that he met dressmaker Marian, now 81, and, after they impressed one another with their prowess at the jitterbug and the jive at a local dance hall, they began dating.
Despite the grey of post-war Edinburgh, for Tommy the late 1940s were a joyful time and the father-of-two performed in the many social clubs that were springing up, delighting audiences at the time by singing and telling jokes.
"Everything had changed after the war, there was a real transition," he recalls. "Edinburgh was a drab, grey city then. Dance halls were dying out but ex-servicemen began running clubs, including the RAF club in London Road and the Jewel in Craigmillar."
A painter and decorator by day, Tommy would rush home to his house in Stenhouse Drive to clean up before going out to perform - first as a solo artist and then as part of a double act with friend Eddie Davies.
And while they were employed time and time again at venues such as the Excelsior Ballroom in Niddry Street, Tommy was also renowned throughout the city for his impromptu performances on buses and trains.
"I've just always loved to entertain, it's second nature to me and I suppose it's just something you have in you," he smiles. "The nights would usually feature an accordionist, an organist, male and female singers, a comedian and a novelty act. Talent-spotters would come along to clubs to watch acts and ask to you to perform another night.
"Then you move up a scale and I started working behind the scenes, organising charity nights and concerts and supplying the acts."
Indeed, for the last 50 years, Tommy has been the man behind hundreds of events in the Capital organised in aid of charities and organisations including St Columba's Hospice and the Sick Kids Hospital. His work has raised funds for everything from Crohn's disease charities to guide dogs and without fail, for the last 50 years, he has organised a Christmas party for hundreds of pensioners in the Capital.
When he was organising his shows, Tommy was not in the slightest bit frightened of reaching for the stars and the famous names he persuaded to come to charity events over the years have included Frank Carson, Paul Daniels, the Alexander Brothers, jazz singer Jackie MacFarlane, Cannon and Ball - then known as the Harper Brothers - and Cliff Richard.
And despite being a lifelong Hibs supporter, Tommy also took his flair for the entertainment industry to rival fans when he did a stint as entertainment manager at the Hearts social club. Throughout the evening he would change outfits before introducing each act, choosing from gold, silver, blue and - suitably - maroon mohair suits.
He laughs: "I got crucified for working there and being a Hibby! Then I organised entertainment nights at Easter Road, and I got crucified there for having worked at Tynecastle!"
Tommy is bursting with energy and enthusiasm and he has no plans to slow down. The only clue to his age is that he is hard of hearing, something that was caused when he was training for the Black Watch and a flash bomb burst his eardrum.
He is currently social convener of the Scottish Pensions Association and works as an Edinburgh Festival guide, taking tourists on walking tours. "I promote Edinburgh and I just can't see past this place," he says. "It is the finest city in the world. I've been to Rome and Paris but there's no place like Edinburgh. It's got everything and the history is incredible, walking down the Royal Mile to Holyrood Palace.
"It was a surprise to receive the award but there really is nothing better than to be recognised in my own city."
Tommy has always worked as a fundraiser for free but he is modest about his achievements. "If something is worthwhile, I will do it right away," he says.
"And I've never asked for anything. Money doesn't come into it. Myself and Marian have never needed anything. She loved her work and I loved mine so we have always understood each other.
"It's great to see people enjoying themselves and you get to know people. It's been worth it for all the friends we've made."
ELSPETH HAS NO SIGHT - AND NO FEAR
DESPITE being blind since birth, Elspeth Brown is fiercely independent and counts skiing, canoeing and tandem cycling among her favourite sports.
She skis regularly at Hillend, where radios are used by instructors to communicate the directions to her.
She also knows no fear of the water and is an experienced canoeist.
Indeed, Elspeth's sporting streak has won her medals and, in her late 30s, she took up tandem cycling with a sighted partner and they entered both velodrome and road racing events in Britain and Europe.
But it is her work as a Girl Guide leader for the past 37 years that has earned her a Lord Provost's accolade as a good citizen. She is currently Ranger Guide with the 135th Unit Royal Blind School, Blackford Division.
Elspeth lives in Fairmilehead and gets the bus each day to work as a support assistant at Leith Social Work Centre, assisted by her guide dog Uska.
Elspeth, 56, says: "As a Guide I try to encourage girls with sight difficulties to do things they don't think are possible.
"I want to show them you can do any activity that an able-bodied person can do. It might take longer to achieve, but it is always possible."
Local heroes are worthy recipients
LAST night saw the presentation of the Sir William Y Darling bequest for good citizenship, which was created and named after the man who was Lord Provost of Edinburgh from 1941 until 1944.
His legacy was to bequest 2500 to the City Chamberlain to reward good citizens on an annual basis - an award that has mainly been awarded jointly over the past decade.
Speaking in advance of last night's ceremony, Lord Provost George Grubb said: "The presentation of the William Y Darling Award gives us the opportunity to recognise individuals who are an inspiration to us all and whose hard work and dedication enriches hundreds of lives.
"Tommy and Elspeth are true local heroes who for many years have brought happiness to many people.
"As great citizens of our city they both deserve the recognition that this prestigious and famous award brings."