I'VE LOST COUNT of how many times Dave and I saw Dirty Work, but it was more than two dumb teenagers—even ones as dumb as we were—should've seen anything. Released in June of 1998, not even a year after Norm Macdonald had been fired from Saturday Night Live, Dirty Work tells the tale of two jackasses and their "revenge-for-hire" business. Those jackasses are played by Macdonald and Artie Lange; they stumble through a narrative in which Chevy Chase gets repeatedly maimed, Gary Coleman asks Satan, "What'chu talkin' 'bout, Satan?" (Satan, natch, is played by Adam Sandler), Don Rickles arranges people in a line so he can more easily insult them, and Chris Farley plays "Jimmy," who lives over at the Y and got his nose bitten off by a Saigon whore.

Clearly, Dirty Work has much to recommend it, but the best thing about it is Macdonald, whose stone-faced deadpan, eviscerating wit, and mischievous smirk also served him well behind the desk of "Weekend Update." Alas, Dirty Work—no matter how many times Dave and I went—became another in a line of vehicles that never got Macdonald the accolades he deserved. There were a couple of forgotten sitcoms, and guest spots that ranged from voicing Death on Family Guy to playing himself on Who Wants to Be a Millionaire? But as was the case on SNL, Macdonald's clever turns and dry delivery can make him a hard sell. Like his Twitter feed—which sometimes offers exhaustive play-by-plays of sporting events, sometimes novella-length stories written with surprising grace and melancholy—you never quite know what you're going to get.

Except, that is, when Macdonald's doing two things: stand-up, and making one of his legendary talk show appearances. It's not hard to see why he's revered by Letterman, Stewart, and Conan: No matter how boring the other guests are, his rapid-fire arsenal of anecdotes and quips never disappoint. The best use of your time at this exact moment—and possibly at any moment—is to watch a blurry YouTube titled "norm saves the interview." I'll wait.

But nowhere is Macdonald more at home than at a comedy club, where his mumbly, rambling delivery masks brutally sharp crowd work and devastating smarts. No matter how much Macdonald tries to downplay it, to see one of his sets is to see not only the funniest guy in the room, but also the smartest. He'll veer into the absurd, or get meta, or go dark, but no matter how bleak the jokes—a few years ago at Helium, he replied to a heckler's fear of clowns by telling them they'd be better served by a real phobia, like choking to death on black bile in the middle of the night—there's a core of earnest, red-blooded humanity beneath them. There's something genuine. Maybe that explains why, even though it's always a blast to see Macdonald be the best part of someone else's show, nothing can compare to his own.