Lindsay Lohan's comeback attempts, from 'Liz & Dick' to that Esurance commercial

When is Lindsay Lohan not on the brink of making a big comeback?

It's been a long and bumpy ride for the actress since her 1998 "Parent Trap" role, full of highs ("Mean Girls") and lows (run-ins with the law, violating probation, rehab stints, etc.). Hearing Lohan say she's ready to launch a project that'll kick her career back into fifth gear — yes, that's a "Herbie Fully Loaded" reference — isn't anything new.

Below, relive some of the star's noteworthy comeback attempts.

Singing of a broken heart

Singing started out as a hobby nearly every one of the characters she portrayed just so happened to be into. See: Anna Coleman's rock band in 2003's "Freaky Friday" and Lola Cep's dream of becoming a star in 2004's "Confessions of a Teenage Drama Queen." Trying to break free from those memorable roles and kick-start her own music career, she released her debut album in 2004. "Speak" was followed by "A Little More Personal" in 2005. The only song of her more than 30 recorded tracks that made even a dent in the Billboard charts was "Confessions of a Broken Heart (Daughter To Father)," which ranked 57th on Dec. 24, 2005.

If you're now looking to shake the depressing image of a heartbroken Lohan crying on the floor of a dirty bathroom in the "Confessions" video, here are a few lines from "Freaky Friday's" "Ultimate" to get stuck in your head. You're welcome.

Sing it with us: "You're it, you're the ultimate. It's automatic I'm sure of it ... You're it. You're the ultimate you."

Taking on a more serious role

After the actress faced some serious tabloid backlash stemming from her on-set trouble during the filming of "Herbie Fully Loaded" in 2005, she decided to take on a more serious role in the late Robert Altman's "A Prairie Home Companion." The film, Altman's last, was released one year after the "Herbie" ordeal. It starred Lohan as Lola Johnson, alongside a top cast of Woody Harrelson, Maya Rudolph, Meryl Streep and Garrison Keillor, seen here with Lohan. The role didn't exactly open up a world of serious acting gigs for Lohan.

Scaring (or scarring) us all in a thriller

Following a list of some pretty wholesome, early 2000s-type movies on her resume, including "Mean Girls" and "Just My Luck," everyone's favorite fake twin decided it was time to shake things up a bit and take the lead role in a horror flick. Unfortunately for Lohan, 2007's "I Know Who Killed Me," didn't open up any big doors for her future in thrillers. The film was named the worst movie at the 2008 Golden Raspberry Awards, known as the Razzies, and she was crowned the year's worst actress for the role.


Expanding her resume

In 2014, Lohan made her professional stage debut in the theatrical production "Speed-the-Plow," a West End revival of David Mamet's 1989 play. While the actress earned decent reviews, her role didn't impress everyone. The Telegraph called the play "workaday but watchable," and wrote that her "flat delivery needs more work, but so does the rest of the show." The Independent called it a "good but by no means a great night out."

'Singing' on a Duran Duran track

OK, so "Confessions" wasn't exactly the last time we saw Lohan try her hand in music. After a nearly two-year break from the big screen after her 2013 role in "The Canyons," Lohan surprised us all with a cameo on Duran Duran's album "Paper Gods." Don't be too shocked, though, she was only given a spoken-word role on the track "Danceophobia" and face time in the music video.

Channeling Elizabeth Taylor

As expected, lots of hype followed Lohan's gig as the late Elizabeth Taylor in Lifetime's made-for-TV movie "Liz & Dick." As Newsday critic Verne Gay wrote in his 2012 review of the flick, "it takes guts for an actress to play Elizabeth Taylor -- guts, hubris, talent, empathy and a pretty generous capacity for risk." Did Lohan have it all? Eh ... it was deemed "not a total disaster" by reviewers and seemed to be a pretty good step in the direction of a "Lohan comeback," but Gay only gave the movie a C-.

Popping up in sitcoms

Though Lohan hasn't been the star of her own successful sitcom, she's popped up as a guest on numerous others. She starred as Kimmie Keegan in a few 2008 episodes of "Ugly Betty," as herself in a 2012 episode of "Glee" and a 2013 episode of "Anger Management," and as Claire Guinness in "2 Broke Girls" in 2014, among other roles.

Giving us a taste of reality

When things go sour, what's better than showing the world you've (supposedly) pulled it all together again than by launching your own reality show. Between partying, arrests for drunken driving and shoplifting, Lohan couldn't seem to keep her mugshots out of the tabloids between 2006 and 2013. In 2014, the actress tried to show the world she was rebuilding her life and career after a stint in rehab with a big move to New York City ... and a reality TV show on Oprah Winfrey's OWN network. The documentary-style show, set mostly in SoHo, ended up just proving how out of touch with reality Lohan, seen here with her mother Dina on the show, was and got the boot after eight episodes following poor ratings.

Poking fun at herself

Perhaps there's something to be said about someone who can turn her lows into the subject of a money-making Super Bowl commercial. Enter: Lohan. The actress was featured in a 2015 Esurance ad driving, yes, driving (and sort of crashing) a minivan. In case you forgot, this was a huge deal being that the actress was arrested and charged with DUI in May 2007 and again July of that same year.

Launching her own prank TV show pilot

Singing wasn't her calling. Horror flicks didn't do it for her. Reality TV was a bust. So what's Lohan's next move? Creating her own prank TV show. The actress released a video teaser of her new "Punk'd"-style show on March 22, 2017 but it hasn't yet been picked up by a network.

Securing a UK acting gig

After a nearly two-year absence from the acting scene, Lindsay Lohan joined the cast of "Sick Note," a British TV production. She'll have a guest role in the comedy's second season and appear alongside "Harry Potter" star Rupert Grint. Shooting in the UK, perhaps we'll get to hear a bit of Lohan's old "Parent Trap" accent. The series airs July 26.

Shamelessly becoming a spokesperson for

Lohan is owning up to her mistakes and the reputation they've gotten her in the most self-deprecating way -- by becoming a spokeswoman for Her face, smiling almost awkwardly, is now the first thing you see when you visit the site.

In a video titled "Why did Lindsay Lohan join," she says she was "confused and a little scared" that she was in trouble when contacted her about the gig, but realized the company helps people find the best representation.

Always the straight-shooter, she acknowledges that we know she's been in deep legal trouble for DUIs.

"Let's not pretend I didn't get one, or two, or three..." she says.

Give fans a dose of reality, take two

Lohan's reality TV experience didn't go so well the first time around for OWN, but the actress seems to think her lifestyle in Greece will be a bit more gripping than her SoHo stint. Bunim/Murray, the same company behind her family's 2008 E! series "Living Lohan," is set to produce her new show for MTV. Lohan is aware you've been dying to know what her life on the Greek island of Mykonos is really like. "Lohan Beach Club" (working title) will reportedly focus on the ins and outs of her club, Lohan Beach House Mykonos. It'll premiere in 2019. She first teased the idea of the MTV reality show in a June interview with the New York Times.