In the 90s he had a run of miniseries and one-shots that were basically monthly and totalling 66 issues. Of you're going to allow Hellboy ... Down the slippery slope you slide!
Probably the only time a character from a gimmick crossover like Bloodlines amounted to anything. Loose Cannon didn't make it to 50 issues, that's for sure! But Hitman made it to 60.
Spider Jerusalem starred in Transmetropolitan for 60 issues as well.
Side note: Does everyone in a Vertigo comic have to smoke? Is it a by-law or something?