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Penge was once a small town, which was recorded under the name Penceat in an Anglo-Saxon deed dating from 957. Most historians believe the name of the town is derived from the Celtic word Penceat which means "edge of wood" and refers to the fact that the surrounding area was once covered in a dense forest. The original Celtic words of which the name was composed referred to "pen" ("head"), as in the Welsh "pen", and "ceat" ("wood"), similar to the Welsh "coed", as in the name of the town of Pencoed in Wales.

Penge was an inconspicuous area with few residents before the arrival of the railways. A traveller passing through Penge would have noticed the large green with a small inn on its boundary. Penge Green appears as Pensgreene on Kip's 1607 map. The green was bounded to the north by Penge Lane, the west by Beckenham Road and the southeast by the Crooked Billet. On a modern map that area is very small area but the modern day Penge Lane and Crooked Billet are not in their original locations and Beckenham Road would have been little more than a cart track following the property line on the west side of Penge High Street. Penge Lane was the road from Penge to Sydenham which is now named St John's Road and Newlands Park Road. There was also an old footpath crossing the Green leading to Sydenham that was known as Old Penge Lane. After the London, Chatham and Dover Railway was built, Penge Lane crossed the line by level crossing. When this crossing was closed Penge Lane was renamed and Old Penge Lane became the present day Penge Lane.

The 1868 Ordnance Survey map shows the Old Crooked Billet located to the southeast of the current location. This earlier location was on the eastward side of Penge Green, which disappeared as a result of The Penge Enclosure Act, 1827 which enclosed the whole Green. This left the Crooked Billet with no frontage to Beckenham Road, so new premises were constructed on the present site in 1827 and subsequently replaced in 1840 with a three-storey building. This was severely damaged by enemy action in World War II and subsequently rebuilt.

The Crooked Billet is by far the oldest public house in Penge. Peter Abbott states that it was there in 1601 and speculates that it might be much more ancient. In modern times it is particularly well known for lending its name as a bus route terminus. From 1914 General Omnibus routes 109 and 609 both operated between Bromley Market and the Crooked Billet following different routes. The 109 was renumbered 227 by London Transport and continued to terminate at the Crooked Billet. (Route 609 was shortened terminating in Beckenham ). Around 1950 some services were extended past the Crooked Billet to the Crystal Palace. Eventually nearly all buses traveled the extended route. The 354 buses now use the terminus, as do so short running buses on route 194 which carry the destination 'Penge High Street'.

William Hone wrote about a visit to the Crooked Billet in 1827 and included a detailed sketch of the last building on the original site.