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I put the comics in chronological order by release date and put some thoughts next to each one along with why you may want to pick up a copy for yourself.  The easiest way to read a lot of these comics for a low price would be to sign up for a Kindle Unlimited Plan (they offer a free trial, link is to the right or below on mobile version).
Pinhead: This is the first Hellraiser comic I can remember reading.  While building this website I dug my old issues out of storage to re-read them.  It was enjoyable to see one of my favorite characters in comic form.

The story can best be described as Pinhead meets Quantum Leap as the soul of Elliot Spencer (modern Pinhead) is jumped through time backwards attempting to stop a rogue Cenobite from destroying the current Cenobites from undoing things from the past.  The coolest part is seeing past iterations of Pinhead in their environment including 1876's Scarred Hide (with embedded arrow heads), 1728's Monsignor (with jeweled nails), 627's Xipe Topec, undetermined date Bel Ala and finally a nameless pre-historic version of him.  Additionally in the first comic there are several alternate versions of Pinhead skins hanging on the Hell Priest's wall.

Not your typical Hellraiser story but it was entertaining. It was also an examples of things I probably shouldn't have been reading as a kid since there are several adult themes and graphics sprinkled throughout the comic.
Pinhead vs. Marshall Law: Not the best comic in the series but it is an interesting story of an anti-hero and Pinhead crossing paths.  Only worth it if you have exhausted most of the other Hellraiser related reading material and are still looking for more. 

Hellraiser Masterpieces:  Masterpieces are shorts stories that tell the stories of more people opening the box or finding hell through another means.  Most do little to expand the Hellraiser universe but provide entertaining and interesting tales.  It kind of reminded me of Tales from the Crypt except all Hellraiser-centric. 

Hellraiser Masterpieces Vol. 1: The best part of Vol. 1, in my opinion, is the introduction of The Harrowers.  The Harrowing story tells how each Harrower found their way to Joplin, MO and ultimately was imbued with power to fight the forces of evil.  Vol. 1 only tells half of the tell though, so you'll have to pick up Vol. 2 to see the ending.

Hellraiser: Masterpieces Vol. 2: Vol. 2 is more short stories like we see in Vol. 1 including the ending of The Harrowing storyline.  Other interesting stories were things like a boxing ring acting as a gateway (The Sweet Science) and the story of one of the Harrowers rescue attempts (The Last Laugh).

Hellraiser Omnibus Vol. 1: If you are going to read one Hellraiser comic, read this one.  I really wish someone in Hollywood would take this storyline and adapt it into a big budget movie like Avengers.  The action is huge, the story is interesting and it really expands on the charecters of both Elliot Spencer and Kirsty.  I started reading this without knowing any of the details and was shocked as the story unfolded.  The really dive into the backstory of Elliot Spencer and your opinion of him will change several times as the story progresses.  It is a departure from the gritty nature of the original movie but for a charecter that has now been seen dozens of times, it brought new life into the story of Pinhead.
Hellraiser: The Road Below:  The Road Below actually takes place some time in the latter half of Omnibus.  With a new Pinhead things aren't always so simple.  Kirsty has to figure out her new role in society.  This was a great story but did little to expand the overall Hellraiser universe.  Nevertheless I enjoyed it a lot.  While not as good as Omnibus or Dark Watch, I liked it better than the short stories from the other Hellraiser comics.

Hellraiser Dark Watch:  Dark Watch picks up where Omnibus left off.  It really expands on the Hellraiser universe in addition to giving us our third version of Pinhead in the modern comics. I would rate Dark Watch as my favorite, right behind the Omnibus.

Hellraiser Dark Watch: Vol. 1: I really enjoyed this one giving a look at the new Pinhead.  It also showed the power of crosses and brought back Tiffany and her new band of Harrowers. 

Hellraiser: Dark Watch: Vol. 2: Picking up where Vol. 1 left off, Vol. 2 continues the story showing a side of Elliot Spencer that is even more disturbing.  The Harrowers step up their game with the use of blessed daggers and blessed crosses to protect themselves against the forces of evil.

Hellraiser: Dark Watch: Vol. 3: The thrilling conclusion to the series and it finally wraps up the story that started in Omnibus and The Road Below.  This book also introduced Abaddon and the part of hell based on fury.  The story still managed to suprise me at the end and provided a nice conclusion to the whole saga.

Hellraiser Bestiary: Bestiary includes more short Hellraiser stories and is my favorite of the short story format of comics.  The Hunted was my favorite, broken into six parts between Bestiary 1-6, it involve a group using crosses to weaken and attempt to kill Pinhead.  I was also suprised to see a refrence to The Desert Father, in a story by the same name, referencing early monks that went into the desert to pray.  This is something well known in the Orthodox Church but is hard to find in modern forms of Christianity that tend to throw out the baby with the bath water after the Reformation.

It also introduced us to other mechanisms of hell, the guitar shown in the story Old Hat to Raise the Devil in book two and the book shown in book five in the story Folie a Deux.  Book four finally brought a solid explanation to the tagline of Angles to Some, Demons to Others in the story And God Will Send His Angels.  Finally, the story Science of Madness brought a look at the box from a scientific perspecitive as a scientist tries to unlock its secrets using modern technology adding further details to LeMarchand's creation.

Hellraiser Anthology comics are similar to the Masterpiece ones.  Not only do they have short stories in comic form but also art, poems and short stories of all text.  

Hellraiser Anthology Vol. 1: One of the more unique stories in here included Pinnochio.  Overall it was entertaining but I thought Vol. 2 was better.

Hellraiser Anthology Vol. 2: Vol. 2's short stories I thought were more intersting.  The Test showed what happens when a monkey tries to open the box. Another Pinnochio story is included along with another kid's toy, "Pokemon" type trading cards that open the gateway.  Other stories inclue The Octagon, which felt like a modern update to The Sweet Science, the boxing-centric stroy from Hellraiser Masterpieces.  Plus, this one also has The Chatterer's backstory in "Prayers of Desire", which is an all text story.

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Hellraiser started out as a novella, The Hellbound Heart.  As a fan of horror or Hellraiser, it seems almost mandatory to read the books.  Here's a couple of thoughts on each of the three Hellraiser novels.
The Hellbound Heart: The Hellbound Heart is the story that started it all.  Just as in the movie, my favorite parts are the begining and the end, which feature the Cenobites.  Overall it is a good book and you'll be familiar with much of the story if you have seen the movie.  Things that will jump out at you include Pinhead being a female (or at least an androdrynous male), a different female Cenobite as the leader and the engineer as a blinding light instead of the weird monster we get in the movie.

Hellraiser: The Toll: This is the only Hellraiser book not written by Clive Barker.  The Toll adds some back story to some of the charecters we meet in The Scarlet Gospels as well as continuing the story of Kirsty.  You don't need to read it prior to Scarlet Gospels but if you are looking for more content, it is worth picking up to give it a quick read.

The Scarlet Gospels: My favorite Hellraiser book by far.  The Scarlet Gospels is a great story with an interesting plot and lots of action.  It includes the Harrowers, Satan, Pinhead going rogue and more.  If there was ever a Hellraiser story that needed to be turned into a big budget Hollywood movie, this is it.  As a Christian who is a fan of horror I was shocked about the number of comments and references Clive Barker made using information from the Church and The Bible.  Overall, it is great and a must read if you are a Hellraiser fan.  

The Scarlet Gospels and The Hellraiser Omnibus are the two things that got me back insterested in the franchhise after not following it for 15 years. 

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This is a Hellraiser and associated properties fan site.  Videos and pictures are property of the original content producer. When possible, it is also meant to educate followers about the Orthodox Church by mixing in fiction (the world of Hellraiser) with fact (Orthodox Christianity).