- Awesome Music: The games are perhaps known best for their cinematic soundtracks before cinematic soundtracks became a common thing, which were both composed by Richard Jacques, with the first game being performed by a live orchestra. While the sequel lacks the live orchestra and has a more ambient feel, it still retains the cinematic touch and certainly isn't without its own memorable songs. Special mention goes to "Jack's Theme", "Greywolf", "Ramirez at Bay", and "Final Conflict" from the first game, with "Perilous Descent", "Recycling Migs", and "Taking Liberty" from the second. It's no wonder the first game's soundtrack won numerous awards and both had a physical soundtrack release.
- Base-Breaking Character: Leeza X, the new protagonist in Redemption. Some felt that her constant snark and sassy attitude came off as forced and made her a very annoying character, while others thought that it made her enjoyable and fun to play as, and felt that she had much more depth than what she let off. Much of the criticism aimed towards her seems to stem from the fact that she's a new character who took the spotlight from Jack. Fortunately for those who find her a Replacement Scrappy, our favorite bearded headhunter becomes playable later in the game.
- Complete Monster: Candy Floss, the Depraved Dentist and Torture Technician, and head of Research & Execution in Redemption, is by far the most unredeemable character in the franchise. His work is first shown when Jack discovers a tortured and mutilated Che, who refers to him as the "diablo", who is Driven to Suicide. When Floss is introduced, he taunts Jack about experimenting on his innocent son before he was sent to Liberty, and explains his past as a dental surgeon who was sent Below for conducting mechanical experiments on children, and resents society for deeming him a monster. While he was able to continue his inhuman experiments Below, he laments that he misses the tears in the children's eyes, the screams of pain, and look of utter fear in their faces. After Jack takes him down, Floss expresses no regrets and taunts Jack further by saying he's lost everything, which includes his missing son, his partner, and his now deceased ex-wife. His Boom, Headshot! was well-deserved as it was relieving.
- Contested Sequel: Fans of the original game are certainly split when it comes to the Darker and Edgier Redemption. Not everyone was fond of Leeza or that she took the spotlight away from Jack, that a major character from the previous game was killed off, the game's stronger emphasis on cinematic storytelling, its overall gloomy mood and depressing story that lacks the flair of the original. On the other hand, the game does have its share of defenders that enjoyed the game and dark sci-fi narrative, finding it to be a worthy follow-up to the original, and felt that adding a new spunky female protagonist was a smart move for the sequel.
- Creepy Awesome: Candy Floss. He's a terrifying character, but that's what makes him a cool villain.
- Cult Classic: The first game in particular is seen by one by many Dreamcast fans, as it came late in the system's life, and while its development was advertised in some US magazines, it never hit the states on the console. Although the sequel isn't as fondly remembered by some fans of the original, it also has its good share of fans and defenders who also consider it one.
- Ensemble Dark Horse: Stella, the sassy L.E.I.L.A. receptionist in the first game due to her exasperated Deadpan Snarker and the great delivery of her lines made her a highlight for many fans. Unfortunately, she only appears in a couple of scenes.
- Evil Is Cool:
- Greywolf, mostly due to his memorable boss fight and his cool attitude. Most people found the Badass Biker gang leader cool before you beat him, and more so when he helps you out later on.
- Candy Floss, for being the scariest and most intimidating villain the franchise has to offer.
- First Installment Wins: Many fans seem to favor the original game over its sequel, due to its memorable bike-riding moments, fun dialogue and humor, unique story, and orchestrated soundtrack.
- Ham and Cheese: Given its influence from 80's action and sci-fi films, the first game's story is widely seen as delightfully cheesy, but special mention goes to the live-action news bits featuring Kate Glosse and Bill Waverly. It's clear both actors are fully aware of the Black Comedy and satirical aspects of the story and are hamming it up as much as they can, adding greatly to the game's humor.
- Hilarious in Hindsight:
- The first game drew several comparisons to Metal Gear Solid for adopting numerous gameplay elements, with some denouncing the game as a clone but with a bearded hero instead. When Metal Gear Solid 3: Snake Eater came out years later, not only did Naked Snake adopt his own beard, but Solid Snake carried the style over in his appearances in the Super Smash Bros. series.
- One of the things people remember most about Headhunter was Jack Wade's beard. Years later, there's a company that sells beard oil and balm, with one of their scents named "Head Hunter".
- Iron Woobie: Redemption is one giant Trauma Conga Line for Jack Wade. He married Angela but they soon got divorced, and his young son was kidnapped by the machines right in front of his eyes. He later comes to her rescue but is too late to save her, and once she falls to her death, he can't watch and immediately turns away, knowing full well that she's already dead. Although Angela told him that their son is alive, when Jack finally discovers him in Liberty, he's a living corpse connected to and being controlled by a computer network. Horrified of what's become of his son and what he has to do, Jack disconnects him puts him out of his misery. A machine later rips his corpse out and uses Chris to fight against Jack, and he has to put his son down again in a boss fight. As cool as he is, Jack is not shown to take these well at all and becomes more broken each time. He pretty much loses everything except Leeza at the end.
- Memetic Mutation: When the first game was released, many people had a field day pointing out Jack's beard as his most distinguishable feature, since most game protagonists at the time were cleanly shaven. This has led to some nicknames such as "Metal Gear Solid 3: Bearded Justice" (years before the actual game hit), "bearded Judge Dredd alike", and more. You can bet that when Redemption was announced, fans were relieved to see that Jack's beard returned intact.
- Nightmare Fuel: The last part of Redemption is filled with this. The halls of Research & Execution have blood on the walls and floor, discovering a mutilated Che, who's completely broken after being experimented on by Candy Floss, and his audio recording that he decided to experiment on her without using anesthetic. There's also his creations, the biomechs, which are zombie-like machines that attack in large numbers. There's also the truth about what Liberty is, a hive mind controlled by the 6808 comprised of countless prisoners having the life sucked out of them, including the reveal of Jack's son being a living corpse.
- Player Punch: Redemption is filled with these. Aside from the details in Iron Woobie above, Che is Driven to Suicide after being mutilated by Candy Floss, and Leeza's dad dies in the ending, after she spent years trying to find him.
- Scrappy Mechanic:
- While the bike segments were seen as one of the first game's highlights, allowing players to drive around town at their leisure, the controls were another matter altogether, and many didn't enjoy the LEILA point system attached to it, restricting players from proceeding in the game until a certain number of points were accumulated with it. While many players were able to overlook the flaws and enjoyed it, the feedback was enough to convince Amuze to remove the bike riding mechanic altogether from Redemption, and fans of the bike segments weren't too happy with this.
- The first game has a Quick Time Event take place against a certain rival before the climax, but unlike many games that utilize it, the buttons have to be held down briefly to avoid the attacks. Let go too early, you get shot and die. Hold it down too long, you get shot and die. Fortunately, it only happens once in the game, but it was known to throw many people off. Others who were expecting the fight to go down in an epic gunfight were also disappointed that the whole thing was over in mere seconds.
- Signature Song: "Jack's Theme". You'll hear it a lot in the driving sections of the first game, it gets a slight remix when you're in the last part of the game, and it gets a reprise in the credits song. It's also remixed in Redemption as the credits theme, which also plays as a Theme Music Power-Up during a specific point in the game when you're playing as Jack again.
- Song Association: Music from both games were featured in the early seasons of Retro Game Master, to the point where several fans of the show who aren't familiar with this series associate "Jack's Theme" with the show itself. Oddly enough, neither one of the Headhunter games reached Japan.
- They Copied It, So It Sucks!: The first game received a bit of this treatment for taking many gameplay elements from Syphon Filter, Resident Evil 1, and most particularly Metal Gear Solid, enough to turn people away from it and dismiss it as a clone. Fans of the game would tell you that this wasn't necessarily a bad thing, as Headhunter took some of their stronger elements and combined them to form a solid, fun, cohesive and enjoyable package.
- What an Idiot!: In Redemption, Jack's son is said to have been kidnapped by the machines and hasn't been seen for years. A flashback shows the moment it happened, when Jack takes Chris to explore a potentially dangerous area.
You'd Expect: That when Jack tells Chris to stay close and not go too far, he'd listen to his dad.
Instead: Chris runs out of Jack's sight when he's trapped in thought, climbing down a ladder into a chasm, allowing a machine to sweep down and snatch him.
Also: Jack himself qualifies for taking his son to such a dangerous-looking place, knowing it wasn't safe to begin with.
YMMV / Headhunter