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.
Next up: Her MTV reality show, "Lindsay Lohan's Beach Club," airing Tuesdays at 8 p.m. The series promises to finally give us a glimpse into the businesswoman role Lohan escaped to in Mykonos.
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 on the leading 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 an 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 in 2017, she decided her next move was to create her own prank TV show. The premise for the series called "The Anti-Social Network," was simple: Lohan would take over a participant's social media accounts for 24 hours, challenging them to take on embarrassing tasks to gain back control of their accounts. The actress released a video teaser of her new "Punk'd"-style show on March 22, 2017, but it wasn't immediately picked up by a network. Plus she was busy landing her next gig.
Securing a UK acting gig
After a nearly two-year absence from the acting scene, she joined the cast of "Sick Note," a British TV production. She had a guest role in the comedy's second season and appeared alongside "Harry Potter" star Rupert Grint. Shooting in the UK, the series gave us flashbacks to Lohan's old "Parent Trap" accent. The series is now available for streaming on Netflix. It hasn't yet been renewed for a third season.
Shamelessly becoming a spokesperson for Lawyer.com
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 Lawyer.com. 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 Lawyer.com," she says she was "confused and a little scared" that she was in trouble when Lawyer.com 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," produced 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. "Lindsay Lohan's Beach Club" will focus on the ins and outs of her club, Lohan Beach House Mykonos. It airs new episodes Tuesdays on MTV, but the early reviews suggest it might not last. Newsday critic Verne Gay only gave it two stars, calling it "dull, derivative and peopled with a cast shrewd enough to know exactly where the camera is and how to perform for it."