The crooked man is reputed to be the Scottish General Sir Alexander Leslie, who signed a Covenant securing religious and political freedom for Scotland. The "crooked stile" in the poem was the alliance between the parliaments of England and Scotland or the border between the two, depending on the source.
There was a crooked man, and he went a crooked mile,
He found a crooked sixpence against a crooked stile;
He bought a crooked cat, which caught a crooked mouse,
And they all lived together in a little crooked house.
The nursery rhyme was first told sometime in the 17th century during the reign of King Charles I. But the Crooked Man was not the Stuart King - it was allegedly inspired by Scottish general Sir Alexander Leslie and the covenant he signed.
The covenant secured religious and political freedom for Scotland despite prevailing animosity between the English and the Scottish.
The crooked stile is the awkward alliance between the two parliaments and the crooked house refers to the collective union the Scottish and English lived together in. But the 'crooked' part works on another level, too.
The great recoinage of late 17th century meant sixpences - which feature in the rhyme - were made of very thin silver and thus easy to bend.
An alternative origins story links it back to Lavenham, a village in Suffolk (England). The half-timbered houses leaned at off angles as if supporting each other, creating a crooked aesthetic that matches the nursery rhyme.