Glenn Wool is like a cartoon character. His delivery alternates between screaming, whispering, ACCents on parTICular syllables, and myriad voices depending on who he’s depicting in a joke. His scruffy hair, facial or otherwise, varies between hockey-player chic, biker dude, and suave gentleman. In some weird way, he doesn’t seem real, but it also doesn’t matter, like the way cartoon characters always wear the same clothing. There’s a suspension of disbelief in Wool’s persona, which may not even be a persona. Maybe he’s just a cartoon character in a human’s body.
Despite his oddly lovable presence, which should indicate to listeners to take his words with a grain of salt, Wool spends a lot of time explaining jokes to his Alaskan audience. How they should react to them. Why he’s not racist after doing an exaggerated Chinese accent (he doesn’t think he’s above Chinese people), how the crowd shouldn’t be sad about him spitting on a boy (he’s not real), and how if they don’t loosen up, he’ll alter his material appropriately (he has a hardcore set, apparently, in his arsenal). In another comedian’s hands, this might be annoying, but for some reason, with Wool it’s not.
Maybe it’s that cartoonishness, or the lack of structure inherent in this, his second album, which are both a boon and a hindrance throughout I’ll Ask Her. A well-timed switch from animated to devious whisper (“Drink it,” he tells a baby and his penis at different points in the set.) is a delightful, laugh-out-loud surprise. But at other times, the voices are grating, if only because they pile up and overstimulate when a regular delivery would have sufficed. The unpredictability is great, because it allows him to go off the rails on a whim, but you get the feeling that if he tightened up his act, it would be one of the best going right now.
Wool regularly brings to mind comic greats both past (Bill Hicks) and present (Kyle Kinane). The way he laughs at his own jokes and holds a playful contempt for his audience echoes Hicks, and his gravelly, often amped-up delivery is reminiscent of Kinane. The combination is a comedy nerd’s wet dream, and adds a certain level of familiarity to his delivery. Like Hicks, some of his jokes go over his crowd’s head, but like Kinane, the Everyman slouch lends a certain balance to the mixture.
Wool is a Canadian by birth, but has spent some time living in London. Currently, he’s effectively homeless, flighting about the world as a “comedy satellite” that perhaps explains why he’s so quick to change voices, go off on tangents and just generally act like his comedy has no home. (An unbelievably silly bit about calling up a terrorist organization butts up against a more serious political thought about Christian history.) He seems perfectly unbound by any sort of reins, which is fine on paper, but difficult to make cohesive in execution.
“Where’d she go?!?” Wool says at multiple times in his set to various characters in bits, calling back to a joke about a booty call gone wrong. As a thematic gag, it works and doesn’t grow old, but it’s an odd thing to thread through a batch of stuff so otherwise unconnected. Moreover, I’ll Ask Her doesn’t feel like an album at all. An informal goofabout? Yes. An easygoing night where Wool interacted with the audience a lot, sometimes necessary and sometimes not, while sometimes prioritizing the jokes? You bet. But it doesn’t feel like he intended this to be released, which makes for an odd listening experience despite several funny parts scattered throughout.
This uneasy flow is perfectly epitomized by the album’s closer. After wrapping up the booty-call bit he’d been teasing out through the whole album, getting progressively irritated at the woman who didn’t show up, he transitions into one final bit. The booty-call joke did well, and considering it’s been dropped in multiple times, it makes sense as a natural closer, a bookend of sorts. Instead, Wool does a cheap gag about Sarah Palin’s presidential run. (Again, he’s in Alaska.) It’s fine as a joke, and it gets some laughs. No reason to fault him for doing the joke in her home state when it was presumably timely and topical. But why include it in an album that’s dropping just months before a presidential race she’ll play no part in? Moreover, why include it at all when you had a good final bit that tied the album together in a way most of the other material didn’t? As ponderous as this decision was, it kinda makes sense that it falls at the end of an album without direction. I’ll Ask Her is a confusing, misguided and occasionally amusing ride, and at its end, that’s the final taste for the listener: confused, amused and weirdly misled. Makes sense, in a way.