Tony Stark’s Worst Girlfriends!

It's gotta be the sex.

Otherwise, what in the name of nanotech would a guy with Tony Stark's looks, genius, fortune and personality have hooking up into any kind of romantic relationship with some of the women that he's been connected to over the years? Just looking at the first volume of his series and our guy's dated mobsters, stalkers and Russian spies.

For someone considered a playboy, our hero seems prone to offer his heart or at least his romantic intentions to women that we may politely call "questionable choices." What follows is my totally biased ranking of Tony Stark's Worst Girlfriends - from the first volume of his series.

5. Roxanne Gilbert. I fully realize that in 1972 Tony Stark's image was in dire need of a makeover. Running a company that made munitions likely had him scoring low on favorability ratings for a good portion of the comic book buying public. As a result, it made perfect sense for incoming writer Mike Friedrich to have Stark Industries ditch bomb-making for more peaceful pursuits. It also made sense for him to move on from Marianne Rodgers (who we'll get to in a moment). But what made zero sense was for Tony Stark to become attracted to Roxanne Gilbert - a woman who came across as his polar opposite in virtually every aspect of his life. She hated having money. She blamed him for the death of thousands during the Viet Nam War. She held herself to lofty standards that allowed her to pontificate those views onto everyone else within earshot - including the handsome and really rich guy trying to date her. As if this wasn't off-putting enough, the "Annoying Hippy" also just happened to be the daughter of decreased former Board Chairman Simon Gilbert - a nasty guy who'd tried to steal his company - and brother of Gary Gilbert - who's villainous alter-ego of Firebrand had damn near melted his armor with him in it!

This confounding relationship ran from #63 until #88, when Roxanne angrily left a luxury NYC apartment that Tony had apparently set up for her - a bold move given that the two of them never so much as hugged one another. Once departed, we don’t see The Annoying Hippy again until #297.

4. Indries Moomji. Yikes! Talk about the worst choice at the worst time! When writer Denny O’Neil needed one final means to nudge Tony Stark off the wagon and back to the bottle, it came in the form of this exotic beauty. Unknown to our guy, Indries had been hired by corporate rival - and winner of Marvel's Lex Luther Lookalike Contest - Obadiah Stane. His orders to her were simple. Make Tony Stark fall intensely hard for her and then destroy him by coldly breaking off their relationship. Although it seems a bit of a credibility strain that a former playboy would be that emotionally vulnerable to a woman portrayed as Ms. Moomji, end result, her rejection kicked the legs of Tony's sobriety right out from under him.

With his boss crashing and burning all around him, pilot - and man no dog was mean enough to bite - Jim Rhodes took over the Iron Man armor. I bring this up because a few issues later, Rhodey caught up to Indries, hoping she could pull Tony out of his rapid downward spiral. She confessed that not only couldn't she help him but that she'd been essentially trained from childhood to be the "perfect woman" that no man could resist. Indries even went as far as to attempt her charms on Rhodey. However, he denied any interest - demonstrating either inspiring inner strength or that he simply could not figure out how to get out of the Iron Man armor at that time.

3. Marianne Rodgers. Aw man. I have a real soft spot for this one. Not only is she the loveliest blonde this side of a Fox News host, but Marianne became Tony Stark’s fiancé in my first issue of Iron Man. Still, this poor woman never stood a chance. Not under the onslaught of excruciatingly bad writing that debuted her as a socialite tossing lines like “Ta, Love” to suddenly and out of absolutely nowhere having ESP powers. Ones that seemed capable only of delivering news that was dire for Tony and/or Iron Man. Still, neither that nor her spending a couple issues decked out in sexy green lingerie as a "demon queen" deterred Tony from popping the question. Unfortunately, despite a huge rock on her finger, her mind ramped things up to Defcon Two with a vision of a really nasty looking cyborg destined to cut Iron Man into salami slices.

The last straw for Tony Stark came when this vision drove her away from him with chest plate was nearly out of power. Yeah, having your future wife run away when all she has to do is find an electrical outlet would tend to sour you on the concept of a future together.

Anyway, as if that wasn’t enough for poor Marianne, she suffered a complete breakdown not long afterwards - necessitating a long stay at a mental hospital on Tony Stark’s dime. We didn’t see those lovely blonde tresses until Round Two of the atrocious Super-Villain War when she appeared at various times, adding immense confusion to an already immensely confusing story and never once even dropping her name. That sent her back to obscurity until writer Bill Mantlo brought her back in #103. Hell bent on revenge against Tony Stark, she instead zapped Midas - a villain who took over Stark International and heart attack waiting to happen. Her reward for ending that overlong storyline was an even longer round in comic book limbo, finally resurfacing in 1995 at the tail end of Volume One with Tony Stark seemingly breaking bad.

2. Whitney Frost (Madame Masque). This one's definitely got to be the sex. Otherwise, I've no explanation why Tony's invested a good chunk of his heart into a woman who's betrayed and even attempted to kill him on a few occasions. What do I mean? Deep breath because this gets complicated.

Whitney starts out in the early days of Iron Man as a bad girl, taking advantage of SHIELD Agent and man posing as Orville Reddenbacher’s lost son, Jasper Sitwell. Following a plane crash that leaves her beautiful face forever scarred, Whitney puts on the gold, becoming Madame Masque.

Later, working for Midas - the same Saturday Morning Supervillain and poster child for Donuts Anonymous that I mentioned above - she kidnaps Tony Stark. After some time together, at his request, she ditches the mask so that the two of them can share a kiss.

From there, they dance around feelings for each other until she confesses to Iron Man that’s she in love with Jasper - an act that leads Tony to calling Marianne Rodgers.

Moving ahead a few years, Tony's new personal secretary - a woman with a name to forever inspire middle school giggling, Krissy Longfellow - turns out to be Whitney! Just in time for Midas to attack! And instead of being pissed off at her essentially stalking him, Tony's totally over the moon with her.

It’s a nice arrangement until she betrays him to aid her father, Count Nefaria - not to be confused with that other similarly dressed Count who sells chocolate cereal. Said treachery and her resuming control of the Maggia, puts quite a strain on their relationship but not her love for our guy.

She shows up every now and then. Whether it’s to confess her love for Tony or to put a bullet between his eyes depends on the writer. Finally, in #248, someone puts a bullet into her, taking that mask for themselves. That storyline goes unresolved until near the tail end of Volume One, a character with that same mask and the longest ponytail in all of 1990’s comics pops up in the later issues of this series along with The Avengers. By the end of that decade, writer Kurt Busiek nicely cleans all of this up, bringing back Whitney Frost and revealing that she used sophisticated androids to serve as Masque and other duplicates of herself. Like I said, there's only one reason I can come up with that explains why Tony’s had her on speed dial all these years.

1. Kathy Dare. After the near Byzantine intrigue of Whitney Frost, this one's pretty simple. Ms. Dare was an unstable hottie who became fixated on our guy. I'm also guessing that our favorite three lettered word had to have a role in all of this. Otherwise, there's absolutely no reason that Tony Stark would allow this enticing little nutjob anywhere near his world. I also suppose part of the blame has to be handed off to artist Jackson Guice for those sexy outfits and poses he drew whenever she appeared. But her every comment screamed, “Danger, Will Robinson! Danger!”

Not to be overlooked, but Tony was also seeing Rae LaCoste - a woman infinitely better suited to his lifestyle and equally easy on the eyes. Worse, our guy had the shallow audacity to even mention his seeing Kathy Dare in a conversation with Rae. I'm guessing it all had something to do with being in SoCal in the mid-80's.

Anyway, instead of exorcising the uber-clingy and exceedingly shallow Ms. Dare from his life, Tony allowed her to continually pop-up issue after issue until she finally shoots him in #242. This launches a particularly depressing storyline with a paralyzed Tony Stark moping around until the departing creative team devised a gimmick that can only exist in the world of comic books to restore use of his legs. Ms. Dare returned a few years later only to take her life as proof that everything that happened in 90’s comics had to be depressing.

With this list being purely subjective, I’m looking forward to your thoughts on it. Let me also invite you to check out my blog, The Iron Age Revisited, where every Friday, I post a review of Iron Man’s first volume. You can subscribe at a link at the bottom of the page.