This page is a wiki. Please login or create an account to begin editing.

Head Over Heels

Your rating: None Average: 5 (2 votes)
Year released:
[www].se [ftp].se [mirror].us [mirror].de
HeadOverHeels10MacOSX.dmg (15.18 MB)
MD5: 48de209cb66b21e85b656be1ab35f5dd
For Mac OS X
[www].se [ftp].se [mirror].us [mirror].de
Guides on emulating older games

This is a free remake for Mac OS X of the original version that was released for various non-Mac platforms in 1987.

The creatures of the planet Freedom are very strange in that they are formed from a pair of symbiotic animals that have adapted to operate either independently or, to their mutual advantage, join together as one - Head saddled on Heels, and indeed these ARE their names.

Head and Heels have been captured, separated and imprisoned in the castle headquarters of the evil Blacktooth empire. Their cells contain ‘keep fit’ equipment, including a wall ladder that Head really must learn to climb. Your job is to get them both out of the castle and into the marketplace so they can join up again. From there, the journey leads to Moonbase Headquarters, where you will have to decide either to try to escape back to Freedom or to be a true hero and teleport to one of the slave planets to search for its lost crown! To overthrow the Blacktooth dictatorship on any of the slave planets would be a major blow to Blacktooth and you could return to Freedom in glory. (From the User Manual)

The game is presented from an isometric perspective, and presents the characters with a number of puzzles involving switches, jumps and climbs. The levels are 3 dimensional, and the characters must collect crowns as they progress. Objects can be picked up and manipulated as necessary. (MobyGames)

See the developer website for other games.

Architecture: PPC

Mac OS X


SkyCapt's picture
by SkyCapt - 2020, December 31 - 12:22pm

Thx for these detailed reviews!

ClockWyzass's picture
by ClockWyzass - 2020, December 31 - 5:48am

I did download and try the 31st anniversary pre-release (version 1.31) on my PowerBook G4 running MacOS 10.4.11, but I haven't played it all the way through to the end (yet).

There are some noticeable differences (relative to the 2003 Retrospec remake):


• This version has no game-speed control and unfortunately the speed with which Head (especially) and Heels moves is very sluggish. However, the game speed is still probably better than any of the original versions on original hardware.
• The keyboard input isn’t handled quite as well at the Retrospec version, so (for example) climbing ladders is much harder because the jump key can’t be held down for automatic repeating.
• The overall quality of the graphics and sounds has a somewhat user-made (rather than professionally-made) quality, in the sense of not being as consistent and refined.


• The graphics settings allow for one of many themes to be chosen, and the variety of themes is quite refreshing. The B&W setting makes it look like the game was ported to a vintage 80s Mac.
• The styling of the graphics closely matches the original versions, but with modern pixel resolution and color palettes. So if you want to know what the rooms looked like before Retrospec transformed them, this is best version to play.
• I don’t know if the sound effects are ripped from any of the original versions, but they sound exactly like you’d expect 80s video games to sound (which is fun).
• There also seems to be more saved-game slots, which could be very useful, given how many saves it takes to complete this game.


Use the Retrospec version to master the game, especially in FAST mode if you can handle it, and use this version to have fun, especially with the themes.

If Doug Mencken is cool with sharing his version, it should be added to the MG downloads.

SkyCapt's picture
by SkyCapt - 2020, December 31 - 3:07am

Did you try the "31A" version? It can be found by websearch the author name plus Head Over Heels. Wondering if 31A has good gameplay, asking the Master...

ClockWyzass's picture
by ClockWyzass - 2020, December 31 - 1:23am

My Head Over Heels mini strategy guide


This game has 7 named realms. Three of the realms (Blacktooth, Market, and Moonbase) have multiple fully- or semi-discrete sections. Market has numerous entry and exit points, so depending on which paths you take during gameplay, it may seem as though Market is more fragmented than it really is. Each of the other four realms (Egyptus, Penitentiary, Bookworld, and Safari) are completely separate from all other realms.


The beginning section of Blacktooth cannot be returned to once it is left. Market is the next sequential realm, but it can be returned to in various ways. Moonbase is the final sequential realm and is the hub from which all other realms are reached. The final section of Blacktooth can be accessed at any time (after reaching central Moonbase), but the endgame destination is located at the far end of this section, so traversing it twice is a waste of effort. The remaining realms can be accessed in any order.


The three essential resources you need to complete this game are: lives, ammo (in the form of donuts), and saves (in the form of fish). In this game, resources (other than moveable objects) are acquired by touching an object that bestows a credit. Touching a white rabbit will give you two more lives; touching a tray of donuts will give you six more donuts; and touching a fish will give you one more save. There are other non-essential resources (namely colored rabbits) that may or may not be worth using. Any moveable objects you need in order to solve the “puzzle” in a room are contained in that room. In this game, objects can never be taken out of a room and used in another room.

The crowns that you need to find at the end of each of five realms are necessary for a complete win, but they don’t have to be carried as inventory items. (They somehow magically transport themselves to the final location.)

Beyond the sometimes exceedingly complicated mechanics of maneuvering through the rooms to move or touch objects, the greatest challenge of this game is to carefully expend lives, ammo, and saves as frugally as possible.


RTFM. If you don’t know what that means, Google it and do it. Unlike most manuals, this one is actually helpful. While you’re browsing the Hinternet, find a good map image and a full (end-to-end) YouTube walkthrough. Most of the resources you’ll find online are for non-Mac versions of the game, but the rooms are all the same (except for some minor changes). If you absolutely love making your own maps, this game’ll give you hours of “fun”. There’s about 300 rooms and many of them are vertically aligned, especially in Penitentiary and Egyptus. If you get hopelessly stuck, your best clues will come from the YouTube video.


Complete the first section of Blacktooth (as far as upper Market) with as many remaining lives and donuts as possible. Practice this by leading both Head and Heels as far into Blacktooth as you can without losing any lives, and then save right before the toughest challenges. Use a different saved-game slot for each subsection of Blacktooth so you have the option of replaying the game from different points. Your goal is to reach upper Market with nearly all of your original lives and at least one spare save.


This step is one of the most complex and confusing of all. There’s a second (lower) section of Market with Blacktooth rooms mixed in, as well as a second (teleporter-isolated) section of Moonbase. Combined, these two sections have a total of five rabbits, one fish, and 23(=10+13) rooms. Even if you wanted to live without the extra save, you need to pass through most of these rooms to get to the core section of Moonbase (where the teleporters to all of the other realms are located).

What complicates these sections is:
• they can be passed through in one of two directions: either upper Market—>lower market—>Moonbase—>central Moonbase OR upper Market—>Moonbase—>lower Market—>central Moonbase;
• once Head and Heels get to the penultimate section, one of the two halves (of Head and Heels) can go directly to central Moonbase while the other will have to take a longer route back through part of upper Market and part of Moonbase to reach central Moonbase.


After joining in upper Market, travel four rooms up to the courtyard and keep going up three more rooms to a drop. From lower Market, split and travel to the right corner, join, teleport, (and optionally teleport twice more to get the white rabbit). From the adjoining room, split and travel left. Heels should travel up and to the left until reaching a teleporter that’ll take it to central Moonbase; Head should travel down and to the left until reaching a teleporter that’ll take it back to Market. From there, Head should travel up and to the right until dropping down to lower Market, and then travel two rooms to the right to a teleporter that’ll take it to central Moonbase. *whew!*

SECOND ROUTE (as an alternate to the first route)

After joining in upper Market, travel four rooms up to the courtyard and turn left into a Blacktooth-style room with a teleporter that’ll take Head and Heels to Moonbase. From there, split and travel right to the far right corner, join, teleport, (and optionally teleport twice more to get the white rabbit). From there, Head should travel down and to the left to a teleporter that’ll take it to central Moonbase; Heels should travel up and to the left to an elevator that’ll take it back up to upper Market. From there, Heels should travel down and to the left (through the courtyard) to a teleporter that’ll take it back to Moonbase, and then travel up and to the left to reach a teleporter that’ll take it to central Moonbase. *double whew!*


Once Head and Heels are rejoined in central Moonbase, use the first saved-game slot to permanently save this location. If you played the game well up to this point, you can use this saved game to practice all of the other five realms. Otherwise, if you have too few lives left at this point, you may need to go back to STEP TWO and improve your “score”.


Repeatedly practice all of the remaining realms. If you can reach the (real) fish in a realm, save the game in one of the last five saved-game slots and use that saved game to practice getting the crown. Always start each practice run from the final Moonbase save.


Once you’re an expert at reaching all five crowns, figure out which realms cause you to lose the most lives. Starting with the original Moonbase save and favoring the realms in which you lose the fewest lives, start playing through the realms sequentially, saving the end of each realm while in Moonbase (with each added realm in its own saved-game slot). If you carefully fill the saved-game slots sequentially and your final “score” isn’t good enough, you’ll have the option of deciding how far back you want to backtrack before replaying the sequence.


One of the realms has an extra fish (aside from the fake fish). Once you get the fifth (Blacktooth) crown, save the game in the last saved-game slot and have fun with re-exploring all of the realms while in safe mode. Once you’re done, restart from the last save and finish the game. While in safe mode, be careful about falling down inside a room without exits. Since you can’t die, there’s no way to get unstuck without quitting the game.


Part of your “score” is the percentage of rooms that you discovered along the way. It’s frustrating when you “win” the game (with all five crowns) but still only have a percentage of 90-something. Here’s some things to keep in mind:
• Many resource items are in rooms that aren’t part of the mostly-linear gameplay path, and you may (or may not) be able to get away with skipping those rooms. Even if you don’t take an item, be sure to peek inside the rooms where those items are located.
• There are a few alternative paths scattered throughout the realms. When building the best version of a saved game (especially in stages), be sure to carefully explore the alternate paths. If you want a perfect percentage score, you’ll have to go out of your way to systematically pass through all possible routes (which involves some backtracking).
• There’re also a couple of rooms that seem to have no purpose at all. It’s possible you may not get credit for discovering a room until you touch the room’s floor. If that’s true, many rooms may be missed because the doorways aren’t at floor level. (I haven’t verified this theory yet.)
• In Penitentiary, you enter the bottom of a vertical sequence of rooms, but the first level has a pathway around the perimeter. That means the lowest level is still below you. However, getting back out of that room is a bitch. If you didn’t know how to stack boxes before, you will by the time you’re done.


Door jambs (and/or casings) in the Mac version are three-dimensional and protrude from the walls, and therefore get in the way of every sideways movement. Learn to adjust for them or die. Getting angry at and/or complaining about the door jambs won’t help you.

If you shoot an enemy (with a donut), the enemy “sticks” to the floor and can’t be moved. However, the effect of the freeze only lasts a few minutes. (I’m not exactly certain how long—I haven’t timed it yet). So, if you accidentally freeze an enemy in an inconvenient location, move Head and/or Heels to a safe location and take a coffee break.

Some colored rabbits add almost nothing to the ease of the gameplay while others are almost essential. For example, in Bookworld, there’s a gorilla dalek that’s a pain to get around, but the red rabbit located four rooms to the left can help you get past the dalek with ease. While the red-rabbit shield is active, immediately drop to the floor, wait for the dalek to make contact, then race to the left, down, and right. Remember to leave a gap for the protruding door jamb, and jump through the doorway the instant it’s reached.

For Penitentiary and Egyptus, be aware that you can still jump from exploding platforms while they are exploding. You’ll never be able to complete these realms without waiting a split second to make the additional jump.

Throughout the game, Heels is cursed with having to evade enemies that track its location (and steer straight toward it). The usual workaround is an odd tracking flaw where when one coordinate-differential value significantly exceeds another, the enemy spontaneously changes direction. In general, since Heels can usually move a bit faster than its enemies, try to have Heels outrace its enemy while in close proximity. Once Heels gets far enough ahead, the enemy will suddenly change direction, thereby allowing Heels to change direction. In most cases, Heels can get to the other side of a room with only two direction changes (assuming the previous change didn’t put it back in the original location). There’s also a bizarre cheat where if Heels races directly toward an approaching enemy, the enemy will chicken out and change direction at the last second (but it doesn’t work with all enemies).

ClockWyzass's picture
by ClockWyzass - 2020, December 29 - 11:58pm

The microcomputer hardware of the 80s simply wasn't powerful enough to handle complex arcade games, so many original games (when played on the original hardware) were extremely frustrating, and for the wrong reasons. Even the same software on emulators can still be a bit clunky. However, this remake is a vast improvement, utilizing the late PowerPC processing capability. The overall movement speed still slows down quite a bit when large stacks of objects are placed on top of a moving object, but the game also offers a "FAST" speed mode that significantly improves playability (once you master the platform acrobatics).

fogWraith's picture
by fogWraith - 2020, December 29 - 10:34pm

I did try to get a response out of the ones responsible for the site, though no answer was ever received. I reckon it's high time we add this to the archive.

WhosIt.There's picture
by WhosIt.There - 2020, December 29 - 9:37pm

Head Over Heels isn't listed anywhere on the developer's website. The link above does go to a "hot" page, but there's no information or download links there. It doesn't look like there has been any update to the website since 2006.

It was one of the most challenging games I’ve ever played

The original on the C64 was impossible garbage - it was very slow and the isometric levels meant trying to control it was extremely frustrating (even when holding the joystick at an angle - same with all the other similar games of that era).

ClockWyzass's picture
by ClockWyzass - 2020, December 29 - 11:58pm

I just finished playing the Mac version of this game (on a PowerBook G4 running MacOS 10.4.11), and I thoroughly enjoyed it. It was one of the most challenging games I’ve ever played, and the (relatively) modern graphics are outstanding.

Compared to a similar isometric hidden-object game from the 80s called “Devon Aire”, I missed the ability to handle objects in a more sophisticated manner (such as being able to pull them), but Head Over Heels still surprises with some very innovative and whimsical arcade-style puzzles. (Some of the platform-jumping techniques are fiendishly difficult).

Even though the Mac version isn’t posted on MG for download, don’t pass this one by. If the true measure of any game is whether or not it can “kick your ass”, then this one is guaranteed to serve you a whopping dish of humble pie… and serve it cold.

Best of all, once you find all 5 crowns, you have the option of re-exploring most of the realms in safe mode. (Just be aware that some areas can’t be revisited once left, some areas are still exclusive to either Head or Heels only, and while in safe mode, it’s possible to get stuck in many rooms and not be able to get out of them without quitting the game.)

This game is available on numerous websites, including macintoshrepository, so it's probably time to bring it into the MG family. Retrospec didn't survive the transition to Intel-processor hardware, so even their remakes are now effectively abandonware. Maybe someday, when a programmer has too much time on his or her hands, they'll port the source code to modern Mac OSs (if it's available).

SkyCapt's picture
by SkyCapt - 2020, October 19 - 4:16am

working in Jaguar 10.2.8
This has, compared to the 1980's 8bit original, added excellent enhanced 32-bit sound and graphics, like what Retrospec is known for doing. There exists another clone of this, made by different folks, called the "Head over Heels 31st anniversary" by "Douglas Mencken" in 2018 which works in Tiger and PowerPC. It isn't as raging as this version but maybe it can be said to more closely resemble the original. Perhaps we should see if "v31A" is ready to be gardenized.