Barry is a train engineer who worked with Dan during his time as a freight train driver in San Andreas and Los Santos for the Go Loco Railroad company.
He assisted Dan in the operating of the train and was capable of driving the train himself should Dan exit the train, a necessary skill due to Dan's accident-prone nature and low attention span. He also helped to prevent Dan from derailing the train, reminding him when sharp corners were coming up so that Dan would slow down, although he may neglect to do this if angry at Dan.
Dan notes that Barry has his back, happy to stop the train or drive the train to his location should Dan accidentally fall out of the train and lose it, however Dan is not sure whether Barry would extend him this courtesy if this happened while he was angry with him.
They seem to have known each other for a long time, they have their differences, which occasionally boils over into arguments, for example in the time we see Barry, Dan notes that he is angry with him for sleeping with his 22-year-old wife, but they also have periods of friendship, such as the time they went on holiday together to Margate, which Dan describes as a 'wonderful time'.
Their time working together comes to an abrupt end, however, when during a routine haul, Dan 'accidentally' punches Barry in the face and kicks him off of the train while trying to sit in Barry's seat. Dan is distraught when he realises what he has done, feeling very guilty for his action. He is so upset and lonely without Barry that he promptly speeds up and derails the train, ending his career as well as his friendship with Barry.
- He sits in his chair in an unconventional manner, leaning back with his feet and hands in the air, according to Dan this is Barry's pastime of pretending to honk invisible breasts when he is bored.
- He is the father of Pensive Man.
- He has a snake tattoo on the calf of his right leg.
- Dan voices suspicions that Barry may be a drug user.
- For the whole time that we see him, Barry is silent, whether Barry is mute, or simply giving Dan the silent treatment, we do not know.
- He enjoys cleaning the wheels of the train, especially when Dan hits an animal with the train, to the point of requesting that he be allowed to do this job.
- He may also appear on the IRL channel, assisting Dan with the filming of a knee-jerk video in lego form, Dan talks to a person off-screen called 'Barry'.