On the CW show “Crazy Ex-Girlfriend,” co-creator and star Rachel Bloom often concealed poignant and pensive introspection behind pitch-perfect genre parody songs like “Settle for Me” (a full Fred and Ginger-flavored dance number), “Let’s Generalize About Men” (reminiscent of pop disco hit “It’s Raining Men”) and apex diva anthem “You Stupid Bitch.”
Bloom’s new live showcase, the one-person-ish musical comedy “Death, Let Me Do My Show,” ventures beyond metaphor by personifying her dread as an actual supporting character, Death.
Played by “Crazy Ex” alum and Broadway actor David Hull, he heckles Bloom and coaxes her, a la Judd Hirsch’s Dr. Tyrone C. Berger from “Ordinary People,” to revisit April 2020. That’s when she lost her friend and creative collaborator, Fountains of Wayne frontman Adam Schlesinger, to COVID-19 and watched her newborn daughter, lungs full of fluid, struggle to breathe in the NICU.
Bloom, who calls herself a “practical atheist, theoretical agnostic,” also musically muses on the concept of death, producing at least one of the cheeriest, most singalong-able tunes about the pet afterlife you’ll hear this summer.
“Death, Let Me Do My Show,” directed by Seth Barrish (“The Old Man and the Pool”), kicks off a limited run at Steppenwolf Theatre Aug. 14 on the heels of a successful off-Broadway stint late last year that included a taping for a Netflix special.
“Doing this show has absolutely helped me reckon with the idea of death,” Bloom says.
Bloom has always danced around darker subjects with a skillful two-step of irony and satire. She first gained recognition in 2010 for writing, producing and starring in the original music video “F- – – Me, Ray Bradbury,” in which she laments how her suitors will never measure up to the science fiction writer from Waukegan. Follow-ups included “I Steal Pets,” “Chanukah Honey” (as in “Santa Baby”) and “Historically Accurate Disney Princess Song.”
These videos caught the attention of screenwriter Aline Brosh McKenna (“The Devil Wears Prada,” “We Bought a Zoo”), who collaborated with Bloom on “Crazy Ex.” The show ran for four seasons on The CW, ending in 2019 and earning Emmys for music (Bloom, Schlesinger and writer Jack Dolgen) and choreography.
On “Crazy Ex,” the juxtaposition of earworm and brain dump enabled Bloom to dig into dispiriting subject matter and unabashedly celebrate mental health with an ensemble number like “Anti-Depressants Are So Not a Big Deal.”
“I think for a lot of [performers], myself included, part of the motivation is about airing trauma and trying to find a mutual weirdness in the world,” says Bloom, who went on to star on Hulu’s “Reboot.”
Bloom’s last few Chicago visits played a part in shaping the narrative of “Death, Let Me.” On April 3, 2018, she celebrated her birthday at Avec with the cast of “Crazy Ex” the night before they performed at the Vic Theatre. The evening morphed into a sweet celebration of Schlesinger when the party retired to Bloom’s hotel room and the cast sang along to “Stacy’s Mom,” his band’s biggest hit. Bloom dubbed him, “Mr. ‘Stacy’s Mom’ himself!” and he laughed as he sang along.
For “Death,” Bloom was mindful to salute Schlesinger and their friendship without veering into sappiness. “There’s never a moment where I play a montage of pictures of Adam and go, ‘I miss you,’ ” she says. “He would have hated that.”
Bloom returned to Chicago in September 2019, after “Crazy Ex” had ended. She was a few months pregnant and touring a new show fittingly titled “What Am I Going to Do With My Life Now?” Some unsettling news arrived before her show at the Chicago Theatre: Her doctor called to tell her she’d been flagged for a rare blood disorder. (The result was later proven to be a false-positive.) Between fear of this new unknown, the high stamina required to perform and a need to prioritize her health, she canceled the rest of the tour, and the Chicago show wound up being her last.
“In retrospect, the experience was almost a harbinger of, like, ‘You’re going to be slowing down a lot more; not touring and not going to Chicago are going to be the least of your concerns,’ ” Bloom says.
When the Steppenwolf residency wraps, Bloom also will have finished editing the Netflix special. She feels Chicago again serves as a natural end point: “I’m very ready for the special to come out, and I’m very ready for Steppenwolf to, maybe, be the last place I do the show live.”