Ravenesque, moonish, moody, glowing eyes with wolfish glint, a lady in black brandishing wit and guitar pick (corresponding with a guitar that, admittedly, isn’t living up to its potential). Karen Kilgariff is the coolest folk hero of the almost-analogue, post-comedy boom collapse era. She came into prominence in the 1990s, starting out in Sacramento, then San Francisco, then introduced (widely) on the seminal Mr. Show. She’s since matched might with Mary Lynn Rajskub as Girl Guitar Club, wrote for the Ellen DeGeneres Show and twisted on the tips of tastemakers’ tongues.
I wouldn’t categorize the comedian’s recent song-centric oeuvre as “musical comedy”. That term conjures up vests or suspenders, pop culture parody or paradoxical genre bending that is as nuanced as a bag of bricks. Karen Kilgariff is more literary, less novelty; more post modern, less meta pomp; more pronounced than stated. Few can do it like Karen, none can do it as Karen.
Live at the Bootleg is definitive. Sure, 2011’s Behind You, her studio-made extended play debut, translated Kilgariff’s sugar and cyanide but it’s two-dimensional by proximity. Live at the Bootleg is incredibly real, inspired, and leaves nothing to the imagination (except for the inherent limitations of an aural medium). Textures— the adoring audience’s energy, “in the room” humor, banter, riffs, mistakes, thanks, breath and brass—convey gravity, a concrete time and space. Karen Kilgariff is best in the moment.
The ultimate irony: the album’s keen, acerbic aphorisms rib the very scenesters marveling at her brilliance. It’s all farce. Contradiction abides. Nothing is safe from spite. In Live at the Bootleg, Karen’s substantial hilarity juts wildly with powerful, jubilant ennui. See, a concise summation is horribly inept; downplays too much work and too much play.
I Want to Win: An ambient overture, a gentle, rustic glade. “Cut the crickets”, states the bard, sets the tone in a hurry. Heart-felt cold shoulder, jesting manifesto from a sincere misanthrope. A mockery of singer songwriters and sour grapes; a parody of parody. Karen, endearing and candid, quips free associatively about her setting and grievances. “I did ask to have the mic[rophone] raised and then tipped down Radiohead style, but apparently they thought I was kidding,” huffs Karen passive aggressively.
Solid 9: Poppy, peppy, optimistish satire, fearlessly prodding insecurities, combating our very vain culture. This song makes a strong case to the album’s intrinsic value: beautifully written snide, audacious quips and poignant, organic lead-ins. “I’m treating this like a ‘Behind the Music’. So, if you don’t want to hear it, get the fuck out right now!” Karen’s cat-like cynicism crystallizes her distain for self-aggrandizing fanfare, despite purporting very laudable observations. Karen’s cat-like lovability lessens the sting of her
Password: Fingerpicking whismy, vulnerable and forlorn, distracted unluckyinlove song. This modern twist on the breakup ballad targets the heart more so than the funny bone.
Chelsea Guitars: As expounded in the previous track, ‘Chelsea Guitars’ responds to the help of broken dreamers employed by music retail. Delightfully deprecating, Karen Kilgraiff apologizes for failings—not faults—in the face of distain. Fake band names and shining shade makes this anti-anthem a pulpy cautionary tale.
Look At Your Phone: Midwest melancholy through coastal folk, incredibly pertinent, amazingly funny. Los Angeles in grayscale—shout out to West Covina—Karen Kilgraiff explores the phenomenon of social disassociation, by, as alluded in the title, looking at a world’s portal without being apart of it.
Business Situation: Rhetorical inquiry into the wasteful world-weariness of our collective corporate nightmare. Chip Pope, the album’s only feature, handclaps his way to infamy. Ultimately, Karen Kilgariff encourages decency with four-chord flamenco flurry.
AOK: An ode to a dating website you wish you weren’t on. This song is oddly idyllic, like, the chorus could be played in the background of a running montage. The rest lambasts the lies and delusion of people desperate for love (or some facsimile).
Gimmie Mine: Anxiously scribed, deconstructionist nonsong; explicit fodder for a beloved chorus.
Jesus Walks: Karen Kilgariff’s calling card; understated and subversive with wild twists of whimsy.
Golly Gee: Heartfelt Daniel Johnston cover. D.J. is an O.G. weirdo-savant, with a flair for idiosyncratic earnest in lieu of virtuosity. Karen, a Johnston disciple, exemplifies the singer-songwriter’s credo of playing unfettered and singing cheeky.
Drink My Way Through Christmas: The album giggle-filled, nearly-blundered encore reveals a charming truth. Behind her bemusing, shrewd façade, Karen Kilgariff is a gushing goof. Bubbling and gracious, stripped down, expansive and expended, Live at the Bootleg is a conduit for love.
Karen is afflicted as us all, she isn’t absolved from the social ills she lampoons. She just lives her life and creates her art with more than average raw conviction, which, consequently, has created a lasting recording in modern comedy’s canon.