Lindsay Lohan vs. Hilary Duff: A Retrospective

I’m no expert on rhetoric or linguistics or chemistry or men, but I do think that all of these apply to the definition of “rivalry.” However, one relationship — one dynamic duo of divas, one pairing of prissy prima donnas — defined what it meant to be frenemies in the 2000s. I’m not talking Brit Brit and Xtina. I’m talking Hilary Duff and Lindsay Lohan. Let the battle royale begin.

Before I go on, let me state the obvious: Both of these girls had a constant, Big Brother-esque conglomerate controlling their every move. No, not their mothers (we’ll get to Dina later). The House of Mouse, aka Disney, was the driving force for these two budding starlets’ careers.

Movies: Ms. Duff’s first movie of the 2000s was game-changing Disney Channel Original Movie (DCOM) Cadet Kelly. Although it was a made-for-TV film, Cadet Kelly was Hil’s first method of abandoning her Lizzie McGuire persona while somehow staying true to herself on the same television channel. If you don’t remember the image of HDuff dancing with scarves at her progressive high school in the opening credits, who even are you?

Hilary’s movie career continued with roles in Cheaper By the Dozen, Raise Your Voice and, wait for it, A Cinderella Story. A solid lineup for Ms. Duff, but it was no comparison to what Lindsay was doing in the cinema world.

Lohan also started off her aughts film career with a DCOM, although not as revolutionary of a flick in my opinion. Get A Clue is good, don’t get me wrong, but all I remember about Lindsay in this movie are her sunglasses. Still, Lindsay shook the earth down to its core with her slew of films afterwards: Freaky Friday, Confessions of a Teenage Drama Queen and Lohan’s magnum opus, Mean Girls. Give LiLo the Oscar already, dammnit!

Lindsay 1 – Hilary 0.

TV: What Ms. Duff is probably best known for, her truly career-defining moment, was a little show that premiered in 2001 on the Disney Channel entitled Lizzie McGuire. Now, it was no That’s So Raven, but Lizzie McGuire tackled some huge issues: bra shopping, mute children and the appropriateness of wearing a bedazzled bandana.

Lizzie kissed the sweet, sweet lips of Aaron Carter for god’s sakes! She even had Bitmoji 10 years before it was a thing. Boom. Now, let’s look at the other side of the coin. Lindsay was on one episode of That 70’s Show. Yikes. Hilly takes this round.

Lindsay 1 – Hilary 1.

Music: This is quite possibly the most difficult round for me to decide on. And hopefully, dear reader, it is for you as well. I’ll start with Lindsay. In 2004, Lindsay gifted our inferior human race with the album Speak. From its Avril Lavigne-inspired pop-punk cover to its sugarcoated beats, Speak is unparalleled. Featuring the song “Rumors,” a song devout fan, Hopkins senior Jane Morris, refers to as “a luxury,” Speak cemented Lindsay as not just a singer, but a superstar.

Hil, on the other hand, dropped Metamorphosis, a crowd favorite in my childhood home. On her hit track, “The Math,” HiDu croons, “If you can’t do the math, then get out of the equation.” Get out of the equation indeed. I’ve got to give them both a point here.

Lindsay 2 – Hilary 2.

Relationships: This category has multiple facets. I won’t just be looking at romantic relationships, but also familial. Hilary had a pretty tame dating life throughout the early 2000s. She was linked to a few lovers, including Joel Madden (now married to Nicole Richie), to spice up her good girl image.

LiLo, on the other hand, takes the cake. After her infamous “sex list” was “leaked” in 2014, the public learned that Lindsay had been with megababes such as Justin Timberlake, James Franco and even Joaquin Phoenix?!

But let’s bring on the real drama. HilBil, to this day, has a loving and supportive family. Her sister Haylie even joined in on the fun in 2004 with Duff sister hit “Our Lips Are Sealed.”

Now, let’s honestly pour one out for Lindsay Lohan’s family. Her father, Michael, is a money-hungry, self-indulgent, overly-tanned kumquat of a human. Her mother, Dina, is also a money-hungry, self-indulgent, overly-tanned kumquat of a human. What a surprise that their marriage was the equivalent of Eddie Murphy’s rap album.

Lindsay’s sister, Ali, attempted to make a career for herself as well (no thanks to Dina) and instead became a failing model in Taiwan. And yet, as heartbreaking as Lindsay’s family life may have been, it’s safe to say that she definitely has not been affected by it at all and is a sober, happy and sane woman nowadays... right?

Lindsay 3 – Hilary 2.

Lindsay Lohan most recently starred in a London West End production of the play, Speed-the-Plow.

So what can we gather after all of this extensive data has been put on the table? With a final score of Lindsay 3 – Hilary 2, we can finally put to rest that Lindsay Dee Lohan owned the early 2000s, and not even Hilary Duff can take that away from her. Forever may she reign.