Winston (Original Timeline)

"Winston's family has been with the Crofts for generations, and he has been the family butler since he was honorably discharged from the military in his late-twenties; just as his father before him. He moved into Croft Manor to stay as the only live-in staff when his wife died, before Lara was born. He tends to all Lara's household needs, going far beyond the duties of a traditional butler given Lara's unusual lifestyle and pursuits, but he has never disappointed her. His loyalty to Lara, her parents, and Croft Manor is beyond question."

Winston Smith has been in every Tomb Raider game. A fun game that was very popular among the fans was locking Winston in the fridge in the original Tomb Raider games, as he always followed you. Run into the kitchen. Open the fridge by using the button. Get inside the fridge and wait for Winston to appear. Then quickly run out leaving him and shut the door again.

Tomb Raider II
In Tomb Raider II he follows you around and also he can be locked in the freezer.

Tomb Raider III
In Tomb Raider III, he follows you in the same way. Later Lara can pick up her pistols at the end of the Assault Course. When these are picked up, Winston will appear in a camouflage suit. You can shoot him, and he will raise his tray in defense.

Tomb Raider: Legend
Winston comes back in Legend. He looks taller and much younger than in the previous games. he appears in cutscenes and the Manor level however he has no dialouge or movement.

Tomb Raider: Underworld
Winston makes another return in Tomb Raider Underworld. The only appearances of him are in cut scenes. One before the Croft Manor level begins where he is seen walking through catacombs with Lara and in another he is seen standing next to a gun-wielding Zip.

Voice Acting
Alan Shearman gave Winston his voice for Tomb Raider games: Legend, Anniversary and Underworld.