Murphy’s Law – Why Lindsay Lohan’s impending jail time is great for her career

Joel Murphy

Joel Murphy

I never realized just how far Lindsay Lohan’s career had fallen until yesterday. Sure, she hasn’t been in a noteworthy movie since Mean Girls and these days she’s known more for her partying, sleeping around and troubles with the law than for her acting. But it wasn’t until yesterday, when Lohan was sentenced to 90 days in jail that I finally saw just how bad things had gotten. It’s Hollywood, for goodness sake – if a judge is actually holding Lindsay accountable for her actions, clearly she is no longer viewed as a celebrity.

And it wasn’t even like Lohan killed anyone (which, for a celebrity in Hollywood typically amounts to nothing more than a stern talking to). No, Lindsay was sentenced to jail time for violating the parole of her 2007 DUI conviction after she missed several mandatory alcohol education classes and failed to appear in court back in May.

Celebrities get DUIs and DWIs in Hollywood all the time and they never end up in jail. In fact, it was just a few weeks ago that Courtney Enlow wrote about January Jones’ reported Bobby Flay-aided drunk driving shenanigans and Jeremy London’s Six Feet Under-esque drug-fueled joy ride. Will either one of those two do jail time? Of course not. And London hasn’t even been relevant since Party of Five went off the air back in 2000. If he’s getting a free pass from the criminal justice system and Lohan isn’t, clearly the future is not looking bright for Lilo.

But as you know, we here at HoboTrashcan are all about finding the silver lining. (Aaron R. Davis even finds a way to put a positive spin on cynicism.) So this week, instead of dwelling on the negatives of Lindsay Lohan’s impending hard time, I’m going to accentuate the positives.

Of course, there are the obvious benefits – like the fact that this could be the kick in the pants Lohan needs to finally get her life together after years of recklessly partying. But, more importantly, this could be a great development for her career … and I’ll tell you why.

Before this sentencing, the highest profile part Lohan was reportedly being offered was the starring role in a low-rent Linda Lovelace biopic, which – after starring in big budget, kid-friendly films like Herbie Fully Loaded early in her career – must have been (ahem) tough to swallow. Besides, I think we can all agree that playing a drug addicted porn star is really not the career boost Lindsay needs. So, with any luck, her stint in jail will force the makers of that film to find someone else to fill the role, helping Lohan to dodge that career-killing bullet.

Even better, it frees Lilo up to do something else once she gets out of the clink. I propose that once she is free from custody, Lindsay should take the lead in a biopic about another trouble, drug-addicted, slutty celebrity – Lindsay Lohan. That’s right, when life gives you mandatory jail time for violating your parole, I say make “mandatory jail time for violating your parole”-ade.

The way I see it, Lohan could turn her troubles into a very compelling trilogy …

The first film would be a 25th Hour-esque story that takes place between today and July 20, the day she has to surrender herself to the court to serve out her sentence. Lindsay could spend her last days of freedom with her friends and her gal, Samantha Ronson. There could be a fantastic flashback scene where Isiah Whitlock, Jr., playing the Cannes cop sent to interrogate Lohan after she misses her May court date, finds Lindsay’s “stolen” passport under her the couch cushion in her hotel room and says, Sheeeeeit! Ms. Lohan, I do believe you’re fucked.” And, of course, there would be the dramatic climax where Michael Lohan (hopefully, still somehow played by Brian Cox) drives Lindsay to prison and offers her one last chance to escape before she ultimately decides to turn herself in.

Once Lohan actually goes to prison, the possibilities for the second film are endless. You could play to her strengths and turn it into a sexy Cinemax After Dark women’s prison story, but that seems a little too easy. (Not that I wouldn’t still want to watch it, of course.) Or you could go the Shawshank Redemption route and have Lindsay one up a corrupt warden by tunneling her way out of prison slowly and methodically – hiding the large hole in the wall using an oversized Justin Bieber cheesecake pinup poster. But I think the best way to go would be something along the lines of The Longest Yard. For starters, Burt Reynolds reason for going to prison in that film wasn’t entirely dissimilar to Lohan’s, so there is some nice symmetry there. Plus, it would be fun to see Lindsay “Wrecking Crew” Lohan lace up her boots to square off against the prison guards in an epic football game, ultimately refusing to tank it even though she knows the corrupt warden is going to extend her sentence out of spite. If nothing else, it’s bound to be better than that unwatchable remake Adam Sandler made.

The third and final film in the Lilo trilogy will be the one that ultimately redeems Lindsay and saves her career. Once she gets out of jail, the judge has ordered for her to spend 90 days in a rehab facility. That means that Lohan can easily turn this portion of her life into an inspirational film about conquering demons, a la 28 Days (not to be confused with 28 Days Later, which is about conquering zombies). We can watch as Lindsay overcomes her addiction and finds redemption in sober living. We will all sympathize with her struggles and root for her as she pieces her life back together. From there, she can go on to do countless cheesy action movies and chick flicks, including a well-received romantic comedy with Ryan Reynolds and Betty White, and ultimately she’ll land a role as a loud-mouthed WASPy mother who adopts a talented, but emotionally-damaged black athlete who goes on to play for the Baltimore Ravens, a role which will land her an Academy Award, but will cost Lilo her marriage to her skeezy biker husband who was secretly banging some tattooed “white power” skank behind her back the whole time. Of course, this will all only serve to make her even more sympathetic and likeable and will even cause everyone to forget about the unwatchable stalker “comedy” she made with Bradley Cooper.

So keep that chin up, Lindsay Lohan. Sure things look bad now, but once you get finished serving that hard time, I think you are going to find that sunny days lie ahead. In no time, you’re career will be bigger than ever and judges in Hollywood will never dare to make you pay for your crimes ever again.

Joel Murphy is the creator of HoboTrashcan, which is probably why he has his own column. He loves pugs, hates Jimmy Fallon and has an irrational fear of robots. You can contact him at

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