It was released in February 1999 as a single from their sixth album, Phantom Power, and has come to be recognized as one of the band's most enduring and beloved signature songs.
The song's narrator works in the city as a police officer, a job he finds stressful and sometimes ponders quitting, but unwinds from the stress and restores his spirit by spending his weekends with a loved one in the rural idyll of Bobcaygeon, where he sees "the constellations/reveal themselves one star at a time" in contrast to the city's "dull and hypothetical" skies that are "falling one cloud at a time".
[5] In the song's bridge, the British rock band The Men They Couldn't Hang are performing a concert at Toronto's Horseshoe Tavern ("with its checkerboard floors"); when they begin to perform their song "Ghosts of Cable Street", which is about the Battle of Cable Street riot in London in 1936, in an "Aryan twang",[6] a similar brawl or riot appears to erupt between fascist and anti-fascist activists in the audience, which then weighs heavily on the officer's mind as he drives back to Bobcaygeon in the final verse.
A common interpretation is that the lyrics obliquely reference the Christie Pits riot of 1933, which arose from tensions between Toronto's working-class Jewish community and anti-semitic Swastika clubs following a baseball game;[7] although the song's otherwise contemporary setting leaves this interpretation in question, a similar albeit less famous public brawl between the Heritage Front and Anti-Racist Action did occur in Toronto in 1993 just a few years before Downie wrote the song.
The song resulted in the town of Bobcaygeon coming to occupy what has been described as a "mythical" place in Canada's collective imagination, as the archetype of a Canadian cottage country paradise.
It was originally recorded for his studio album Daredevil, which consisted entirely of Tragically Hip covers, but was held back for the follow-up EP.
[17] Longtime Blue Rodeo guitarist and mandolinist Bob Egan, who was retiring from music and performing his final show with the band that evening, had been a guest musician on the original Tragically Hip recording of the song.
[20] In 2018, Canadian indie folk band Reuben and the Dark recorded a cover of "Bobcaygeon" as a charity single to benefit the Gord Downie and Chanie Wenjack Fund.