If you think the title of Jay Flewelling's autobiographical extravaganza Please Underestimate Me is meant to be self-deprecating, think again. As Flewelling explains when the show commences, he relishes being underrated because it puts him in an uncanny position of power. The less people expect of him, the more he delights in demolishing their preconceived notions with an unexpected and unambiguous victory.
That credo would sound hollow and arrogant coming out of the mouth of a mediocre performer. But Flewelling is anything but that. The adaptation of his memoir of the same name is a testament to his talents—the ability to delicately soul search with delirious goofiness. Most of all, though, it suggests Flewelling's faith in his abilities is thoroughly justified.
The staging of Flewelling's personal essays comes with a many-faced twist: Not only does he portray himself, but so do five other performers under the direction of Jason Rouse. Dressed in dark T-shirts that have "JAY" emblazoned across the chest in bright white letters, the actors journey across the expansive stage at Portland Playhouse and through the seasons in Flewelling's life—from his traumatic experiences coming of age as a gay man in a conservative Christian community to his emergence as the indomitable performer he is today.
There's something wondrous about seeing people of varying ages, sizes, races and genders embody one man—especially since they are working with the uproarious writing of Rouse and Jessica Dart, who adapted Flewelling's memoir for the stage. While Please Underestimate Me is brutally honest about the suffocating oppression Flewelling faced as a child, the show spotlights his gift for finding sharp slivers of wit in agonizing moments, as evidenced by a scene in which he interrupts a prayer spoken in tongues by singing about Liza Minnelli and Neapolitan ice cream.
Yet Please Underestimate Me is at its most commanding when it jettisons the cushion of comedy. Many of the show's most searing passages feature Scott Engdahl as forbidding figures in Flewelling's world, including his father and a monstrous eighth-grade teacher appropriately named Mr. Fier. The scene in which Mr. Fier viciously mocks middle-school-age Jay's penchant for theatrical gestures is horrifying, even though you can feel the satisfaction Flewelling gets out of transforming childhood humiliations into cathartic art.
Please Underestimate Me lasts an hour, which is its greatest weakness. There are moments when you feel the tension between the Flewelling who wants to entertain and the Flewelling who wants to relive and transcend excruciating memories. Another hour would have given him time to do more of both.
That's another way of saying Please Underestimate Me 2 would be welcome. If we're to get that sequel, however, avoid lavishing praise. In the interest of honoring Flewelling's belief in the power of low expectations, perhaps the best thing to say would be, "No one will show up. And it definitely won't be a brilliant follow-up to one of the year's most delightful and touching theatrical works."
SEE IT: Please Underestimate Me is at Portland Playhouse, 602 NE Prescott St., pleaseunderestimateme.com. 7:30 pm Friday-Saturday, 2 pm Sunday, Aug. 10-12. $15.