The four men posed for the press photographers outside court following their conviction for siphoning diesel from a lorry.
One of the gang, Daniel Warrender, 23, who lives on benefits, poked his tongue out and thrust his hands into the air as he was sentenced to community service.
Warrender appeared alongside brothers Colin Robson, 23, and Luke, 20, and Philip Bailey, 39 at Telford Magistrates Court.
The gang, from Telford, Shropshire, admitted theft from a motor vehicle on Tuesday.
The court heard the four were caught trying to siphon diesel from a lorry at Wrekin Farmers in Allscott, Telford, on March 8, by attaching a car battery to a pump.
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But officers swooped on the business after they were spotted on the firm's CCTV and were tracked by a police helicopter Police found them nearby hiding in an outbuilding, the court heard.
Magistrates were told all of the men, with the exception of Luke Robson who works as a mechanic in Telford, are unemployed and live off benefits.
They were each sentenced to 80 hours of unpaid work in the community and ordered to pay £128.75 each in compensation and costs.
Clare Butler, representing the men, said: "They accept that they took the diesel for financial gain."
One witness said: "They all bundled out of court laughing and joking before a couple of them posed for pictures on the steps of the court.
"They looked more like Lottery winners than criminals. They clearly had no respect for the sentence they were given. It looked more like they were on a lad's holiday."