Go figure. You have the largest single-day event of the year, attracting more tourists than Caribana. You've got more and more queer musicians who are out and making it in the mainstream. You have a vibrant local club scene and musical talent that was the envy of many in-the-know visitors to the North By Northeast festival.
So why is the music on the Pride Stage always so weak? How many community choirs and singers with guitars can a music lover can put up with over two days? And why aren't more live venues scheduling music that fits the Pride spirit?
Mark Smith asked the same questions last year when he came to a Pride Committee meeting. Whether he regrets it will depend on what happens this weekend. He's now the volunteer in charge of coordinating the music for the Pride sector.
It's the first time someone combining major experience in the music business with a decent knowledge of queer music is at the helm. Expectations are high.
Smith, a former club owner, manager and A&R guy with past ties to Enigma Records and EMI, quickly learned why things didn't work out so well in the past.
"The budget is beyond low, and every aspect is volunteer," he says bluntly.
This year, artists like the Indigo Girls and Me'shell N'degéocello play within days of Pride Week. But to include mainstream acts at Pride, Smith says the committee needs more money and better networking -- mostly better networking, and sooner.
"Look at what TV stations like Showcase are doing this week, and the CBC and Bravo. I don't see why live music clubs can't get more involved around this time of year," he maintains.
To that end, he and Lyn McNeill have collaborated to bring (ex-Communard and Bronski Beat) Jimmy Somerville to Lee's Dance Cave on Friday (June 23) and Smith's working on incorporating the El Mo's queer/ glam/punk Vaseline night into the Pride package.
While Smith looks at the bigger picture, there are about a million smaller details to deal with. He has to program close to 50 acts on the main site in a way that makes sense given the events of the day and in a way that makes the artists happy.
This last is not easy. Performers have consistently beefed about having to get their stuff up, do a set and get their equipment down in 40-minute hunks for sums of money that can only be called paltry. As for the pleasure of playing -- which is all that's really left -- it's hard to sound even half good when you don't get to sound-check.
But Smith can't do anything about that. You can try to do a check at 11 am in the morning, but what you hear then won't be anything like the sound when close to a million people are in the street.
He is trying an experiment to improve the situation. Instead of clustering speakers near the large South Stage, he's putting them along Church north almost to Maitland so the sound will be thrown back further and with better quality.
There are also plans to have a DJ system halfway between Wellesley and Carlton so DJs can spin between bands' sets.
But Smith warns that Pride's bigger problems won't be solved until programs can be conceived of years in advance.
"You have to spend at least a year just looking for sponsorships. Next year I want to know my budget beforehand and go out and get people like Boy George."
As for calling N'degéocello right now to invite her to come to T.O. a few days early to play, try finding a hotel room.
"The Pansy Division guys are staying at my house," Smith sighs.