The Very Best of Lindsay Lohan

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SHOCKING NEWS: Lindsay Lohan is in trouble with the law again! Yesterday, after a will-she-or-won't-she-make-it-to-court frenzy, LiLo arrived super late to an explosion of glitter and walked away with a plea bargain that involves 90 days of lock-down rehab on top of 30 days of community service and 18 months of therapy. Maybe this will be the help she seems to need. Instead of rehashing her past faux pas, let's take a stroll down memory lane to a not-so-distant past when Lindsay was at her best.

Bill Cosby Jell-O Collabo

A good way to start your career is to collaborate with Bill Cosby (just ask Raven-Symoné -- who later went on to be Lindsay's roommate!). In this Jell-O commercial, several kids get jazzed about the new grape flavor, but none of them perfectly embody hip-hop swag like little Lindsay.

Parent Trap

Once you get past the outrage over parents treating ginger kids like popsicles (you take one, I'll take the other), it's pretty impressive that young Lindsay convincingly played two roles at once and faked a British accent and then faked faking a British accent (so meta!). This movie was made for days when you don't feel the need to leave your house.


In this made-for-TV movie that you should watch right after reading this post, Lindsay Lohan's character, a tomboy who likes to play football, is given a doll because breaking gender norms is bad. Then, things get really weird when a spell to resurrect her dead mother turns her doll into Tyra Banks instead (apparently, yelling at girls on America's Next Top Model is not all that she's good at)!


Technically, this isn't a great song, but it's the perfect time-capsule of the mid aughts, a time when every female celebrity was working on laying down some tracks when not too busy finding the perfect olfactory blend for their perfumes or "designing" separates for their fashion lines. Recently, a morning news show cut to commercial break by playing "Rumors" and Lindsay's reaction was golden. A little less enthusiastic than my own when I randomly heard the song at a Brooklyn club last year.

Freaky Friday


This is where Lindsay's rebellious streak is foreshadowed. Her character is mean to her mom (uh oh), has dyed hair (a sign of devil worship), thinks she's punk (as if), and lusts after boys with motorcycles (I bet they don't brake for animals). Turn back, Lindsay!

Mean Girls

This cult classic is the apex of her career so far, which has more to do with Tina Fey's writing than anything else, but still. In an unfortunate instance of art imitating life, Lindsay, like the character she plays, transforms from likable ingenue to self-involved brat. The best way I can think of to celebrate this movie and Linds at her very best is through a moment of gif-watching silence.