"I can't even" may be a millennial catchphrase, but it seems Bob Dylan got there first a half-century ago. As Chris Willman points out in his Billboard review of the newly released Bootleg Series box set, the scene took place during a January 1966 recording session as Dylan grew frustrated at his band's takes on the song "She's Your Lover Now." He complained that it was "ugly," adding, "I can't. I can't even." Wonders Willman, "Did Bob Dylan just invent the 21st century catchphrase 'I can’t even'? I think he did!" The not-so-serious assertion has prompted some others to consider the question. In a language blog at Slate, Ben Zimmer cites another's blogger's observation that "I can't even" reflects a "stylized verbal incoherence mirroring emotional incoherence," and observes that Dylan "was certainly experiencing emotional incoherence" at the time.
Dylan's "I can't even" wasn't as "stylized" as the modern version, he notes, citing this Saturday Night Live skit as an example of the latter. Still, "it’s also easy to draw a straight line from his use to this one," writes David Graham at the Atlantic. "It’s a clear ancestor. In other words: It turns out that the new Bob Dylan turned out to be … Millennials." Of course, how you'd draw a line from 1966 lament to modern phrase is a little tricky—"She's Your Lover Now" didn't see the light of day until an earlier set of bootleg recordings was released in 1991—but Dylan "has been influencing culture for decades, so it's not entirely outside the realm of possibility," writes David Britton at the Daily Dot. If nothing else, he seemed at least to be ahead of his time on it. (Linguists also are taking note of this modern grammatical shift.)