Richie Ryan was an orphan, a foundling, and a thief in Seacouver. He broke into Duncan's antique shop a few weeks before his 18th birthday. He was 'surprised' when the owner came at him with an old Japanese sword, threatening to cut off his head. He was more surprised when two other men (Slan and Connor) with swords fell through the roof. He ran, right into the arms of the police.

The store owner didn't press charges, but intimidated Richie into keeping silent about what he'd seen. Richie, of course, was fascinated and started following Duncan. He saw Duncan finish what had started in the antique store and behead Slan Quince. He was 'adopted' by Duncan and Tessa not long after, and learned the truth of immortals. Mid year, they moved to Paris.

After the trauma of Darius' death in Paris, Duncan, Tessa, and Richie returned to the states, where they uncovered the Watchers. Tessa was kidnapped by a renegade Watcher; Pallin Wolf. Although Duncan rescued her, she and Richie were gunned down and killed by a mugger on their way back to the store. Richie woke to find Duncan cradling Tessa's lifeless body, and himself immortal.

Later Richie and Duncan 'ran into' Annie Devlin. She was about to kill a british ambassador. Richie stopped her, and killed her husband. She swore revenge, and Duncan began to train Richie. Richie was able to disarm her, but wasn't able to kill her. After that encounter Duncan gave Richie his first sword. His initial training was with a katana, but the sword Duncan gave him was a Spanish Rapier.

Richie moved out of the loft after he beheaded immortal bounty hunter Mako. Mako was chasing Laura Daniels, who was wanted for the murder of her husband. When Laura pulled away from Richie to continue to flee, Mako ran her over, and killed her. Richie was enraged. When Duncan arrived and tried to stop the fight, he was obviously unsuccessful. It was Richie's first Quickening, and the event that, apparently, prompted Duncan to tell Richie it was time for him to find his own path. (And get out of the loft).

An immortal known as Hyde found Richie in France, where Richie was racing. Their initial encounter was in a gas station. Hyde had killed the store's owner, and his wife saw Richie with a drawn sword and her dead husband. She drew the obvious conclusion. Richie left and went to Duncan in Paris. Duncan recognized Hyde as an immortal who used younger immortals to lead him to their teachers.

When the police arrived Richie tried to run but was caught and jailed for murder, leaving Duncan to prove his innocence - and deal with Hyde. Duncan did both by setting up Hyde. Hyde later killed himself and escaped the morgue. Duncan and Hyde fought, Duncan won, and Richie and Duncan renewed their friendship.

Donna, a girl Richie dated briefly several years ago, returns with her 18-month-old son -- who she claims is Richie's! While MacLeod reminds him that it's impossible, that Immortals are unable to have children, Richie sees this as an opportunity to have the family he never had and never will be able to again.

When Kern, an evil Immortal, rides into town, MacLeod is reminded of his own foster son, Kahani. Kahani and his Sioux Indian mother, Little Deer, were massacred over a hundred years ago by U.S. soldiers led by Kern, then a mercenary scout. MacLeod is eager to even the score.

When Donna finds Richie's sword and demands to know what it's for, Richie is at a loss to tell her. MacLeod advises Richie that it would be safer and kinder to Donna and the baby to leave them. When his new-found family is threatened by Kern, Richie realizes MacLeod is right. While MacLeod rids the world of the evil Kern, Richie lets go of the only family he'll ever have.

When Richie 'died' while racing his bike in france, he had to flee the country. Duncan gave him a passport. He got kidnapped by Ivan Kristov before he left the country. Kristov attempted to use Richie to get Duncan to kill Tasha. Duncan arrived to save Richie and started dealing with Kristov's men. Richie untied himself, challenged Kristov- and won.

Richie ran into Mikey Barret in Greenville. Mikey was a mentally challenged immortal. He took him back to Seacouver to protect him. He found a place for Mikey in a religious school, where he'd be on holy ground. When the cops come looking for Mikey about the murder of a woman and Mikey accidently kills one of the cops it all goes to hell.

In the end Duncan and Richie decided that there was no way they could keep Mickey safe from mortal authorities and immortal headhunters, and decide the only thing they can do is kill him. Richie takes him into the tunnel. When Mikey sees Richie draw his sword he puts his head on the tracks, and it's the train that beheads him, are Richie gets the quickening.

After the he ran the dojo, and made his own life; let Duncan fight his own battles for a while. He spotted Tessa's killer out on the street and pursued him. The man wasn't arrested, but Richie jogged his memory and left the reformed junkie with the knowledge that he was a murderer.

When he accompanied his foster mother's daughter to a modeling agency he met Kristin Gilles, an immortal. Both Methos and Duncan tried to warn Richie that the woman was bad news. Richie didn't listen, of course. He was in love and living his own life. When she went psycho-jealous-hosebeast and tried to kill his foster-sister Maria, and himself, neither he nor Duncan could take her head. Methos did. Methos as Adam Pierson, a watcher. The Waters believe Richie took her head.

Richie returned to America with Duncan to meet an old Indian Chief Coltec. Coltec had just taken a dark quickening, and only Duncan's quick intervention saved Richie. When Duncan received the dark quickening he fought his student. This time it was Joe's intervention that saved Richie.

Richie ran, faith broken. He decided that it was all about The Game. He began to train frantically and devoted himself to headhunting. He traveled across the country on his bike, feeding himself with racing and betting. He provoked and fought any immortal who crossed his path.

When he returned the following fall he was still picking fights with any immortal who crossed his path. Joe warned Duncan to watch him, and that Joe was walking an edge. After he killed 900 year old Carter Wellan with relative ease and no reason beyond The Game, Carter's friend - Clay - came after him. In that fight Richie's sword was broken. He asked Joe for help, and Joe refused. So Richie broke into a museum to try to steal a weapon.

Duncan bailed him out when he was arrested, and gave him a sword; one that belonged to an old teacher of Duncan's, Graham Ashe, who had been killed by Clay. Richie and Duncan rebuilt their friendship, this time as equals, and Richie stepped aside so Duncan could settle his score with Clay. Duncan defeated Clay and offered to let him walk, but Clay refused and accepted his death.

When Jennifer Hill came to Seacouver she was looking for Duncan to avenge her husband's death. She was 'haunted' by his ghost. Duncan went to San Francisco to honor his vow to Alec and take the head of the immortal Gerard Kragan, who they thought killed Alec. Richie looked after the grieving Jennifer.

They felt a mutual attraction - much to Joe Dawson's horror. Joe told Richie it was he who had killed Alec. Richie had only known him as an unnamed immortal. He had killed him the summer before, when Alec had picked a fight with him. Alec had been on his way to kill Kragan, in a bad mood, and tried to take it out on Richie when his bike got in the way. Unfortunately for Alec, Richie was in a bad mood too after Duncan's attack on him. Fatal road rage.

Despite knowing this, when Jennifer came to Richie's apartment and tried to seduce him, Richie was unable to say no. He said later he felt like something was pushing him to be with her. It was theorized by Joe that this might be the effect of Alec's Quickening within him.

However, the moral complications plagued Richie's conscience, and he felt the need to confess. First to Duncan, who reluctantly forgave him. Then to Jennifer, who oddly enough did not. She felt used and abused, and went to Duncan to get him to kill Richie. When the Highlander would not kill his friend, she went back and shot Richie, then was about to kill him with his own sword. Duncan got there in time to talk her out of it. With the agreement of Alec's ghost, Jennifer let Richie live.

By the time a new immortal came to town with a message of peace, Richie was more than willing to hear it. He broke up a fight between Duncan and Culbraith, Duncan doubted his worth as a teacher; when Richie said he'd gotten this message from Methos he was enraged. Methos turned up at the loft, amused that the 'other Methos' was in town.

This 'message of peace' had cost several converts their head and Duncan didn't want Richie at risk. So when Methos showed up at the lost, Duncan convinced him to reveal his identity to Richie. Richie, being Richie, said it was the message he believed, not the messenger. Duncan, we're sure, banged his head against a brick wall for a while.

Methos found his impostor, confronted him, and decided not to kill him. Culbraith had no such problems. He found him, and after taking his head tried for Richie. Since Richie had given up his sword he was nearly successful. Duncan saved him before Culbraith is successful and returned Richie's sword to him. Richie won.

Richie left Seacouver and made his way back to Europe, using the name of Richard Redstone. After a decidedly unusual courtship with Marina LeMartin, (she kidnapped him and tied him to her bed) it seemed he was about to settle down. But a night at the Opera with Duncan was a prelude to disaster.

MacLeod swore he saw James Horton on the quai by the barge that night. At first reluctant to believe, Richie found himself defending Duncan to a skeptical Joe and Methos, but then he saw Horton holding a gun to Joe’s head. After telling MacLeod where they were, he went in to try and rescue Joe, unaware that what he had seen was an illusion.

He came upon Duncan fighting invisible enemies. From Duncan's point of view, he was fighting a demon calling itself Ahriman, which had taken the form of his great enemies Horton and Kronos. And that of his student, Richie. Before Duncan could distinguish illusion from reality, he struck, taking Richie’s head.

Joe and Methos appeared and found Duncan kneeling over Richie's body. Duncan and Methos both disappeared, leaving Joe to bury Richie with his sword.