Leeds Crown Court heard 20-year-old Keiran Grant and Aidon Murthick, 19, threatened one man at gunpoint during one robbery, wore clown masks during another and also launched a random attack on a man as he was parked up in Leeds and tried to steal his car.
Grant, of Oak Avenue, Garforth, and Murthick, of Grange View, east Leeds, robbed a 21-year-old man after Murthick arranged to meet him in Leeds on December 12 2016.
Prosecutor Christine Egerton, said Murthick contacted the victim on Grindr using the username Daryl and arranged to meet for sex on Roundhay Road in Leeds.
When he got there, Murthick got in the man's car before Grant - who was wearing a balaclava - opened the door and pointed a handgun at the victim.
Ms Egerton said: "He told (the victim) to get out of the car and lie on the floor. He said this while he was pointing the gun at him and he asked for the keys to the car and for money."
The victim managed to escape the pair who stole his car and drove way at speed.
Police found the car abandoned the following day.,
Three days later, just before 8.30pm on December 15 2016, a 25-year old man was sat in his Audi A3 on Roundhay Road when Grant, Murthick and another man attacked him.
He was repeatedly punched in the face and the third man, who was not traced, repeatedly struck the victim's legs with a mallet .
The three men fled empty handed after that attack.
Murthick arranged to see a man he met on Grindr using the fake profile At 3am on January 9 2017 in the Boggart Hill area of east Leeds.
Ms Egerton said the victim was directed to an address and when he arrived the two men, who were wearing clown masks, ran at his car.
One was carrying an item wrapped in a white towel, which the victim believed was a gun, while the other carried a shovel.
Ms Egerton said one of the pair told the victim: "Give us the keys or I will shoot you."
Grant and Murthick stole the man's car and were caught following a police chase along Wetherby Road.
Grant admitted robbery and possessing an imitation firearm in connection with the December 12 2016 incident while Murthick admitted robbery and possessing an offensive weapon.
Both defendants admitted attempted robbery after the December 15 2016 incident and both admitted robbery in connection with the January 9 2017 attack.
Grant also admitted handling stolen goods worth £6,600, which were taken in a burglary at an house on Farrar Lane, Adel, in July 2017.
Michael Collins, for Grant, said: "He is remorseful for his conduct. The role he took was directed by others higher up the chain."
Giles Bridge, for Murthick, said his client and Grant were childhood friends,.
Mr Bridge said Murthick had been in care from his early teenage years, adding: "At the time of the offences he wasn't in work. He was effectively homeless and receiving very little support."
The Recorder of Leeds, Judge Peter Collier QC sentenced Grant to eight-and-a-half-years in a young offender institution and Murthick to seven years.
Judge Collier told them: "People thought they were coming to meet you for sexual activity of a consensual nature.
"When they arrived they were attacked or threatened by you. The objective was to steal their cars."