Daniel Martin and Daniel Mason have both been in prison for around 10 years after being locked up for separate gun crimes.
They agreed to speak on camera at the prison near Wolverhampton to encourage schoolchildren in the West Midlands not to follow in their footsteps.
Their stories have been posted on YouTube and will be shared with students in schools in Birmingham, where both men are from.
Martin, aged 40 and from Handsworth, was handed an indefinite jail sentence in 2011 for gun possession, robbery and conspiracy to commit GBH.
In 2009 he was one of four armed robbers who targeted a Staffordshire garage and beat up the owner with a baseball bat and shot him as he tried to escape.
And in 2011 he was one of three men convicted after a sawn-off shotgun was fired into a man's home.
Martin doesn't know if – or when – he will be released.
WATCH Daniel Martin's story:
He said: "I was up to no good as a teenager. I was proud of being from Handsworth but proud in the wrong way [being in conflict with people from other areas].
"Most of my ‘friends’ back then are dead or in jail now. No-one comes to visit me and I’m locked up for 23 hours a day.
"I have a 19-year-old daughter and I miss being a father. I’ve missed out on her growing up. There are loads of cells here for you if you go down the wrong road."
Mason, aged 36 and from Northfield, has been behind bars for almost 10 years for his part in a drive-by shooting in Manchester in 2010.
He was jailed for 20 years after being found guilty of possession of a firearm with intent to endanger life.
He didn't pull the trigger, but was convicted under joint enterprise having driven gunman Andre Chiverton from the West Midlands on the night of the shooting.
WATCH Daniel Mason's story:
The shooting, which injured a 17-year-old girl and 20-year-old man, was said to have been a revenge attack after Mason's Audi TT damaged in an Asda car park in Manchester.
Mason said: "I was in a Cat A prison with guys who are doing 20, 30, even 40 years. They were the baddest boys but they’d appear in the morning with red eyes. They’d been crying.
"They knew it [their life] was finished.
"I was getting distracted in school, being jack the lad, I didn’t get a good education and was kicked out of college after getting into a fight.
"I started to hang around with gangs, friends who were making money. I was loyal to the wrong people.
"Those people I thought were friends don’t come to see me in prison . You need to drop people like that. These people don’t care, I’m forgotten about. It’s all fake with gangs."
Birmingham Police Sergeant Helen Carver thanked both men for taking part in the project.
She said: "The videos will be shown in schools across Birmingham from this month; they will be shown in small workshops, alongside mentoring, with the aim being to encourage children to make good life choices.
"These are really powerful messages from people who know what it’s like to get drawn into gangs and crime… and the shocking, life-changing consequences."
Both offenders are part of a mentoring scheme which seems them visit detainees in Young Offenders Institutes to offer support and guidance.
West Midlands Police and Crime Commissioner David Jamieson, who funded the project, said: "It’s so important we find new and innovative ways to reach out to young people to prevent them from being drawn into violence.
"This initiative sees two inmates, convicted for some of the most serious crimes, actually work with the police to get the right message across.
"I’m delighted the two men agreed to tell their story from behind the prison walls, in order to deter other young people from committing similar crimes.
"There’s a real problem with violence in the West Midlands, and across many other parts of the country, and I hope this video can play its part in helping to keep our young people out of harm’s way."