George Condo arrived a generation too late. He belongs to the immortal class of New York artists who revitalized painting in the early 1980s—artists such as Basquiat, Keith Haring, and Elizabeth Murray—back when painting (and the city itself) was going through dark days. But Condo is closer in kind to the mid-century painters who seemed to exhaust all the possibilities of modernism.

The Way I Think, a comprehensive show of Condo’s drawings on view at the Phillips Collection, underscores that elemental truth about the artist. He is deeply invested in Picasso, and specifically, in the painterly one-upmanship in which Picasso engaged with his friendly rivals, Georges Braque and Henri Matisse. His drawings are studied and formal, rarely sketches or doodles, and they reveal a mind working out a problem. The Phillips shows how the methodical madness of Condo’s portraiture developed over time by showing just about everything that happened along the way.

It’s one of the oddest shows that the Phillips has ever mounted: Instead of a curator pouring over Condo’s drawings to draw out a theme or chronological grouping, the museum instead invited him to simply showcase his drawings. So the show—which occupies just three galleries, or maybe two-and-a-half—is chockablock with drawings in all manner of media. The presentation reveals Condo as a diarist and maybe an obsessive, although any artist might come across that way if a museum simply opened up its archives for inspection.

At the Phillips, his drawings are hung salon style. Willy-nilly might be more accurate. There are about 150 pieces in all, covering more than 50 years of production, from a series of dinosaur drawings from 1965 to a drawing from earlier this year (“Constellation 2”). A religious study, “Crucifixion” (1962), is probably his first artwork. And there’s hundreds more at the museum in the form of sketchbooks—stacks and stacks of them laid out on a table under glass.

There are individual standouts among the frames hugging the walls, among them “Wile E. Coyote” and “Foghorn Leghorn” (both 2009), from a series of Looney Tunes drawings that look like eroded wheatpaste posters. They’re a pop art departure for an artist otherwise focused on the figure. Although these drawings do look sinister—which links them to dozens and dozens of reclining nudes and odalisques and other forms of women.

Condo’s signature is a sort of Cubist snarl, a way of scrunching the features of a subject’s face into tightly grouped geometric parts. One untitled pastel from 2013 is an abstract amalgamation of eyes and ears. His faces are locked in cries of anguished passion, as if he’d caught his subjects fucking or dying or bursting into tears. Condo shares the twisted sense of humor of Philip Guston, who painted squat Ku Klux Klan figures smoking cigarettes and painting still-lifes. But Condo’s strategic, relentless, almost competitive approach to the figure and face is pure Picasso. (So are the protests that viewers may raise about works such as “The Discarded Human” (2013), an ink and charcoal drawing of a nude woman in fishnets, her body twisted impossibly, her face frozen in slack smile, her head almost completely dislodged from her body.)

It may be Condo’s relentlessness that draws out a certain instinct in curators. The New Museum, in its 2011 retrospective of the artist, also hung a suite of his paintings, salon-style. It works for the Phillips in the main-floor galleries, the paired rooms where most of his smaller drawings are on view. But an upstairs collection of larger format pieces fails. These are drawings that look like paintings, and they need more room to breathe.

The sketchbooks and journals really do offer a glimpse into how Condo thinks. One notebook is open to a letter, dated 1983, in which he despairs over how badly he needed the $50 check that just found him. There are crude calculations of rents, debts, costs for supplies, the kind that everyone jots down when they’re feeling productive (or worried). One page with a note, dated August 27, no year given, 4:30 p.m.: “I felt better than I have ever felt in my life.”

Who can say that? A day in Richmond last summer stands out for me, but declaring one day, going all the way back? Sketchbooks are a ledger for tracing a life. Condo’s ledger is complete and profoundly focused. Perhaps he knows for certain.

At The Phillips Collection to June 25. 1600 21st St. NW. $10-$12. (202) 387-2151. Phillipscollection.org.