The Highlander films were largely hit and miss, with the seminal original being the only one that has really lived up to its reputation. From its loins came a very unexpected spinoff TV series that won numerous awards, and continued the Highlander story in an alternate timeline from that of the first film. The principal star of the show was Duncan MacLeod, played by Adrian Paul.
Throughout the series' six seasons, MacLeod squared off against numerous immortals who were out for his head. When the show ended, MacLeod's journey continued into feature films beginning with Highlander: Endgame, which continued the storyline of the TV series and gave him a few more deadly opponents to fight.
Updated on July 23rd, 2021 by Derek Draven: With news of a possible Highlander reboot in the works with Henry Cavill in the lead role, longtime fans have plenty to get excited about. The franchise has been a cult hit for decades at this point, beginning in the 1980s with Christopher Lambert in the original Highlander film. The popularity of that film eventually gave way to a spinoff TV series featuring his clansman Duncan MacLeod, who embarked on his own immortal adventures. Throughout the course of the show, and the subsequent films that continued the story, Duncan MacLeod faced off against the deadliest immortal opponents imaginable. This list has been updated to include five more that proved to be his most challenging.
Kenneth
This unique immortal was born in 1172 in England and lost his life at age 11. He was resurrected and taken under the wing of Amanda, who acted as his protector. With no physical strength or skill to protect him from other immortals, Kenneth used his child-like innocence to catch them off guard and slay them.
In later years, Kenneth would be taken under the wing of several immortals, only to betray and kill them all, taking their Quickenings. He then attempted to do the same to Duncan and Ritchie but failed. He would later enlist the help of immortal Terrance Kincaid, who also had a personal vendetta against MacLeod. He managed to slay Kincaid, which left him in a weakened state. Kenneth seized the opportunity but was interrupted by his former protector Amanda, who assured him that she'd kill him if he took MacLeod's head.
Byron
Byron was one of the few immortals to be based on an actual historical person - 19th-century bad-boy poet Lord Byron. It is revealed that Methos mentored Byron following his untimely death in 1815, but it wasn't enough to set him on a path of righteousness.
After Byron influenced an up-and-coming guitarist into joining him in his irresponsible lifestyle (which led to his quick death), MacLeod decided to take him out. The two engaged in a duel in a cellar, where he was swiftly killed. In the end, Byron's excesses and selfish pursuits could no longer be tolerated.
Gavriel Larca
Born in 1438, Larca led a life of piracy before becoming a conquistador, and later a Messiah figure to a tribe living in Peru. Fashioning himself a deity, Larca would later be killed by his own tribe after they began dying of a foreign virus. For 150 years, he lay trapped in a tomb, only to be released in 1980.
Larca quickly took up his old occupation as a cult leader, this time recruiting other immortals into his fold. He successfully convinced them that Duncan MacLeod was the embodiment of Satan, who needed to be fought. Eventually, the two squared off, and Larca easily lost his head to Duncan's superior skill. His true danger lies in how easily he could corrupt and radicalize his followers.
Grayson
Grayson was an immortal born in AD 325 in Dacia, who lost his life when the Goths invaded. Their leader Darius sensed that Grayson was immortal, and became his mentor. Under his tutelage, Grayson wanted to create an unstoppable army of immortals who would put the Game aside in order to rule the world.
When Darius became a changed man and turned into a peacemaker, Grayson became furious and vowed revenge. He began killing Darius' loved ones in an attempt to lure him off of holy ground. MacLeod stepped in at Darius' request to defeat Grayson. He accepted the challenge and nearly killed Duncan, before suffering a beheading.
Slan Quince
Slan Quince helped kick off the Highlander TV series as the first evil immortal to challenge Duncan on screen. He was played by actor Richard Moll, best known for playing Bull, the burly bailiff with a very weird name in the sitcom Night Court. He tracked Duncan to his antique store and tried instigating a fight, only to be stopped by the arrival of Connor MacLeod, who managed to drive him off.
Later, Slan would threaten Tessa's life several times before demanding Duncan meet him at Soldiers' Bridge for a duel. Connor intervened to challenge him but was shot through the heart with a spring-loaded dagger from Slan's sword hilt. Duncan jumped into the fray and slew Quince once and for all.
Otavio Consone
The Spaniard known as Otavio Consone was once a student of legendary immortal Ramirez, who trained Connor MacLeod. As such, he was a gifted swordsman with an intricate knowledge of battle techniques and psychological tactics. He took Duncan under his wing and taught him advanced sword skills before the two fell out over a woman named Theresa.
After a duel that nearly ended in his death, Duncan was spared after Theresa agreed to marry Consone. Three years later, she was thrown down a flight of stairs by Consone in a fit of rage. Duncan squared off against Consone but ended up getting run through with a sword. However, he pulled himself forward along the sword, which surprised Consone long enough to be beheaded with a set of daggers.
Kanwulf
The immortal known as Kanwulf had a long history with Duncan MacLeod, being the first immortal the latter sensed after being resurrected as an immortal. Their feud dates back to 1624, when Kanwulf slaughtered many citizens of Glenfinnan in a raid, including MacLeod's father Ian.
Duncan got revenge, stabbing Kanwulf to death without realizing what it meant to be immortal. Centuries later, the two would reignite their feud over an axe that Kanwulf believed was imbued with magical powers by the Norse Gods. MacLeod gave him his axe back and engaged in a fight, killing Kanwulf and permanently ending their feud.
Liam O'Rourke
This immortal was born in 1883 in Dublin, Ireland, and went on to become a terrorist who once attempted to enlist Duncan MacLeod. After a pub bombing, MacLeod fingered both O'Rourke and his accomplice Tara Fitzgerald for the crime. The two were sent to prison for life, where Tara died.
Blaming MacLeod, O'Rourke escaped prison and kidnapped Amanda and Joe Dawson, demanding his head in exchange for their lives. Methos intervened long enough for MacLeod to avoid a beheading but was shot to death in the process. After reviving, MacLeod and O'Rourke squared off one final time in the Berly Train Depot, where the latter lost his head. It was the final duel of the Highlander TV series.
Haresh Clay
The story of Haresh Clay goes far beyond just a simple fight between two immortals. Clay had managed to best and kill a man named Graham Ashe, a master swordsman who trained the legendary Juan Sánchez Villa-Lobos Ramírez, known to fans for his portrayal by the late Sean Connery, in one of his wackiest roles.
Clay was a man with a vision of how the Game was to be played, and he took no pity on his opponents, nor did he expect any. After Duncan's friend Ritchie Ryan got on his bad side by beheading one of his friends, Clay pursued vengeance. Duncan knew how skilled a swordsman Clay was, and stepped in to end the feud, once and for all.
Xavier St. Cloud
The immortal known as Xavier St. Cloud was cursed with a complete and total lack of conscience. He was taught about his immortality by Henri St. Cloud, only for his pupil to repay him with betrayal. He was both a thief and an assassin who pursued wealth and power through any means necessary.
His first fight with Duncan MacLeod resulted in the loss of his arm, which he replaced with a prosthetic. He then joined forces with renegade watcher James Horton to exact revenge, only to lose his head by his own sword, wielded by Duncan in a final pitched battle.
Antonius Kalas
One of the most evil immortals ever to face Duncan MacLeod was Antonius Kalas, born in Rome in AD 369. Kalas and his mentor Paul created a Christian sanctuary where immortals could flee the Game and live in peace. This gave Kalas an opportunity to slay these immortals whenever they stepped off of holy ground, further increasing his power.
Later, Kalas enacted a plan of vengeance against MacLeod over a past encounter, killing his friend Brother Paul, and planting drugs in Joe's bar to frame him. He then forged medical prescriptions which led to the deaths of several patients in order to ruin the life of Dr. Anne Lindsey, MacLeod's girlfriend. Next, he orchestrated MacLeod's "death" within view of Anne, which caused him to flee to Paris in order to protect her. Finally, Kalas got a hold of the Watcher database of immortals and used it to draw MacLeod. He lost his head, and the Quickening ended up destroying the database, robbing Kalas of his victory.
Jin Ke
Highlander: Endgame was the first film to directly continue the story of the TV series, picking up not long after the final sword had been swung. The story revolved around a rogue immortal named Jacob Kell who cheated at the Game at every opportunity, gaining immense power in the process. As such, he was able to intimidate a number of immortals into his service.
One of them was Jin Ke, played by legendary martial arts star Donnie Yen, known for his extraordinary fight scenes in the Ip Man franchise. Jin Ke had served Emperor Qin in the 3rd century BC, and was one of the deadliest immortals in existence. He and Duncan fought with weapons, barely managing to keep pace with one another. The fight then switched to hand-to-hand combat and ended in a draw, earning each other's respect. Jin Ke would later be betrayed and murdered by Kell, simply for his power.
Connor MacLeod
Christopher Lambert was the original MacLeod, the one who started it all in the 1986 film Highlander. He was one of the most powerful immortals in all of existence and defeated some of the deadliest and most evil opponents, notably the vicious Kurgan. That Quickening gave him massive power which would be needed for the battle yet to come.
The tragic story of Connor and Duncan began with the revelation that the former had taught the latter everything he knew in order to survive. When Jacob Kell became too big a threat to contain, Connor forced Duncan into a fight so that one of them would gain enough power to overcome him. In the end, Duncan reluctantly beheaded Connor, taking his power.
The Guardian
Most fans wish to forget the abomination that was Highlander: The Source, which was the final film that would wrap up Duncan MacLeod's saga. Nevertheless, the immortal he faced in that film was far different from any he'd encountered before, and it was a battle tied directly to his own destiny.
The Guardian was a former immortal imbued with incredible powers and tasked with protecting the Source of Immortality. He proves to be the deadliest immortal in existence, dispatching several of MacLeod's allies before the two ended up facing each other down. This immortal was unique in the fact that he wanted to lose to Duncan, in order to pass on his Guardian curse, and finally be free.
Jacob Kell
Of all the immortals that have come and gone, Jacob Kell is undoubtedly the deadliest. His centuries-long quest for vengeance against Connor MacLeod eventually spilled over into the modern day when he began targeting Duncan, as well. Kell's immense power came from the sheer number of heads he took over the years, which imbued him with immense strength, stamina, and skill.
After Connor forced Duncan to kill him in order to absorb his power and level the playing field, Duncan engaged in one final battle with Kell that nearly cost him his life. In so doing, Duncan became one of the most powerful immortals in existence, if not the most powerful.