The yobs used knives, a crowbar and a screwdriver to slash tyres, smash windscreens and dent bodywork during the eight-hour rampage, a court heard.
Dozens of car owners woke up to find their vehicles wrecked following the orgy of destruction that caused £21,000 in damage.
Tyron Cotterill, 20, Lewis Watts, 22, Adam Guy, 23, and Kieran Painter, 18, were each jailed for eight months.
Tyron Cotterill was involved in the £21,000 wrecking spree
Lewis Watts joined in with the vandalism
Adam Guy was with the group which visited different towns
Kieran Painter was part of the eight-hour wrecking spree
The vandalism spree took place in Leicestershire on New Year's Day between 10.30pm and 6.30am and spanned 25 miles.
Cotterill, from Beaumont Leys, Leicester, and Watts, Guy and Painter, from Melton Mowbray, admitted six counts of criminal damage.
Leicester Crown Court Recorder Justin Wigoder told the defendants the scale of the vandalism was "quite remarkable".
This sports car was one of up to 86 vehicles attacked
The driver's window of this motor was broken
A tyre the gang slashed on the New Year's rampage
The gang broke a hole in this saloon's back window
He said: "You embarked on a spree to cause criminal damage over much of this county.
"I don't know why you all decided to do this, whether it was because you intended to damage one car and then damaged others simply to cover your tracks - or whether it was the sheer enjoyment of hearing the glass smash.
"What's quite remarkable is the length of time this went on for and the number different cars that were attacked.
Another car which was targeted in the spree
A hatchback with the rear window put through
Tyres were burst and windows were broken on this 4x4
"The schedule shows 21 different villages.
"The car owners will have woken up the following morning to find their windows smashed and tyres slashed and on occasion dents to bodywork.
"It's no consolation that they were insured because they would have had an excess payment."