What does crookedest mean?
"Crookedest" is the superlative form of "crooked," an adjective describing something that bends or curves the most — a road with sharp hairpin turns, an old tree with gnarled branches, or a picture frame hanging noticeably off-kilter. Because "crooked" also carries a well-established figurative sense of dishonesty or corruption, "crookedest" likewise extends to people and institutions: the crookedest politician, the crookedest deal in town. The word is informal in tone, appearing more often in conversation, journalism, and travel writing than in formal prose, where writers may prefer "most crooked." It is perhaps best known from tourist lore surrounding Lombard Street in San Francisco, frequently promoted as "the crookedest street in the world." Vivid, colloquial, and instantly understood, it adds color when precision about extreme bending or dishonesty is needed.
Most bent, curved, or twisted; superlative of crooked.
"The old oak's crookedest branch still held a tire swing."
Most dishonest or unscrupulous (informal, figurative).
"Voters finally ousted the crookedest councilman in the city's history."
San Francisco's famously winding Lombard Street is often called 'the crookedest street in the world' — though Russia's Dunedin claimants might argue otherwise.
Reviewed by Deb Chak, Editor. AI-assisted content curated by RJS Tech Solutions LLP.
Etymology of crookedest
"Crookedest" derives from "crooked," the past participle of "crook," which entered Middle English from Old Norse "krókr," meaning "hook" or "bend." The Norse word shares Germanic roots related to hooking and curving. From its literal sense of something hooked or bent, "crooked" developed the figurative meaning of dishonest by the early modern period, and the superlative "crookedest" followed as a natural inflection.
Related word forms
How crookedest is actually used
Informal register; the comparative 'crookeder' and superlative 'crookedest' are common in speech but some style guides prefer 'more crooked' / 'most crooked' in formal writing.
Easily confused with crookedest
'Crookedest' means most bent or dishonest, while 'cruelest' means most cruel or causing suffering.