Jen Kirkman is a thinking person’s comedian. Not by being hyper-intellectual—although she’s a fiendishly smart writer and performer—but by doing comedy for people who live inside their own heads. Her best routines take a thought and follow it to any and all conclusions, no matter how neurotic it makes her sound or how insane the eventual conclusion winds up. It’s a skill that’s carried her through two comedy albums—2006’s Self Help and 2011’s Hail To The Freaks—and allowed her to build a successful podcast, I Seem Fun, on the sole conceit of just sitting alone in bed and saying what’s on her mind.

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The opening routine of Kirkman’s latest special, I’m Gonna Die Alone (And I Feel Fine), follows that idea perfectly, as she relates overhearing someone order a drink and realizing that he can’t tell the difference between lemons and limes. From there it’s disbelief over the way the bartender patronizes him (“The bartender just starts naming green fruit, and I’m like ‘What’s happening?! …to our country’”), terror at the thought that this guy might have someone’s 401(k) in his hands, and a desire to call Homeland Security because she’s seen something and needs to say something and the directions on how to do that are unclear. This eventually builds to a moment of total darkness, where she admits that it may not be the worst thing if he was drugged and didn’t wake up: “And we have one less fucking dumbass on the planet. Wouldn’t that be nice?”

After that, the material slides into the fully autobiographical, where Kirkman is at her best. On the heels of her 40th birthday and her 2013 memoir, I Can Barely Take Care Of Myself: Tales From A Happy Life Without Kids, I’m Gonna Die Alone, Kirkman is hashing out thoughts on being divorced and childless in a culture that doesn’t know how to deal with either of those things. The end result is a nicely discursive hour-plus of standup, one that covers familiar topics but stands out due to material that sounds bitter without being embittered. As the title implies, there’s no regret to any of this, just the feeling of getting a bunch of frustrations off her chest before the effort of thinking about them too much drives her crazy.

The strength of that approach also relies on Kirkman’s most dependable skill: a complete and total openness when it comes to her most mortifying moments. A detailed routine about her unintentional experience being a cougar is a centerpiece of the special. “Don’t look up to me with this story, but learn from it,” Kirkman says at one point, a message that could be applied to much of her comedy. She’s without pride or shame in these exploits, merely offering humiliations to the audience to take as they will.

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Similarly, there’s no hesitation in letting an audience in on her difficulties with masturbation, her need to craft the narrative taking her down the most macabre routes: “I cannot masturbate to a penis in the woods!” Director Lance Bangs furthers the personal aspect of I’m Gonna Die Alone by never taking the camera off Kirkman, with no cutaways to the audience at any point. We’re not here to see people be mortified when Kirkman talks about having gray pubic hair or eating a block of cheese like a sandwich. We’re here to watch the way these realizations play over the comedian’s face and see just how she’ll react to the experience.

When the jokes move toward the broader topics of the experiences she’s missing out on—wedding registeries, parenting tactics, etc.—things become slightly more insular. Kirkman turns into an anthropologist of cultures she finds strange at best and horrifying at worst. She takes friends to task for activities like lurking in their children’s bedrooms or trying to un-invite her from a couples’ dinner, but her anger isn’t directed at them, but at the societal norms that made them act this way. It’s a comedy of incomprehension, looking at the way these lives are lived and why they make no sense from Kirkman’s perspective. (The bracketing sketches, opening with a friend who brings their child backstage and closing with an elderly couple disappointed by Kirkman’s cynicism, emphasize the disconnection she feels by being comfortable with her situation.)

Kirkman ends the special with an affectionate look at her grandmother, who ended her life living up to the special’s title: 99 years old, cursing her late husband every night, found clad in a black bra and nothing else. “Not even Amy Winehouse died in such a fucked-up outfit,” she narrates, clearly seeing a freedom worth emulating in all the darkness. That sense of freedom in a situation that society pities runs through I’m Gonna Die Alone. Its unapologetic and thoughtful-to-the-point-of-neurotic worldview shows Kirkman at her best.

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