Lohan was a child model from the age of 3 and appeared in several television commercials as a child. At the age of 10, she starred in the soap opera Another World and made her big-screen debut a year later, in the 1998 remake of The Parent Trap. Taylor starred in her first movie, 1942's There's One Born Every Minute, when she was 9. She became a breakout star at the age of 12 with her performance in National Velvet.

In National Velvet, Taylor plays Velvet Brown, a tween who masquerades as a jockey and rides her horse to victory in the Grand National steeplechase. Lohan became a household name after 2004's Mean Girls, which explores the cliquey relationships among high school girls and the effects cattiness can have on young women's body image and self-esteem issues.

Lohan's parents, Michael and Dina, finalized their divorce in 2007, but that didn't put an end to their drama. As recently as October 2012, Michael called the police to Dina's home in order to break up a fight between her and Lindsay, and the three subsequently engaged in a war of words about everything from Dina's alleged drug use to Lindsay's financial situation. Lindsay has also publicly feuded with both of her parents. Taylor's mother, Sara Sothern (a retired actress herself), was quite a stage mother, forcing Taylor to practice her acting skills for hours a day at the expense of school. When a teenage Taylor told her mother she wanted to quit show business, Sothern told her she had "a responsibility" to her family, her country and the world to stick with it. Sothern also facilitated engagements or near-engagements for her daughter with Howard Hughes and football player Glenn Davis for financial or publicity reasons.

In interviews about her childhood, Lohan has said that she often felt the burden of having to raise her younger siblings while they were growing up. Lohan's troubles began in 2004, on the set of Disney's Herbie: Fully Loaded, when the then-teen was hospitalized with a kidney infection due to stress in her personal life and was involved in the first of what would turn into a slew of car accidents. She began attending Alcoholics Anonymous meetings in 2006 when she was 20. Taylor, meanwhile, spoke about having trouble befriending children her own age because of her stardom, and began landing highly sexualized roles at the age of 16. She married her first husband, Conrad "Nicky" Hilton, when she was 18.

Taylor was famously married eight times to seven men. (She married and divorced her co-star Richard Burton twice). Besides Burton, Taylor's spouses included hotel heir Conrad "Nicky" Hilton, Eddie Fisher, and U.S. Sen. John Warner. Lohan's public relationships included dating Aaron Carter in 2003 and That '70s Show star Wilmer Valderrama in 2004. Her breakup with Valderrama is said to have contributed to the "personal issues" Lohan blamed for her hospitalization that year. In 2007, she dated British TV personality Calum Best. In 2008 and 2009, she dated DJ Samantha Ronson and the two were tabloid fixtures throughout the course of their tumultuous relationship.

In the late 1950s, Taylor began dating her late husband Michael Todd's best friend, Eddie Fisher, while Fisher was still married to Debbie Reynolds. Reynolds eventually forgave Taylor and the two went on to star in the 2001 TV movie These Old Broads. Lohan and Hilary Duff simultaneously dated Aaron Carter in 2003, and Lohan accused Duff of "stealing her man" (even though Carter and Duff began dating in 2001). Carter eventually broke up with Lohan and resumed dating Duff, but the couple split later that year. The actresses reportedly officially ended their feud in September 2012.

Taylor and Lohan both posed for Playboy, the former in 1963 and the latter in 2012. Taylor was one of the first celebrities to pose mostly nude for the magazine, a tradition Lohan continued nearly 50 years later. Lohan's shoot was inspired by Marilyn Monroe's pictorial in Playboy's first issue.

Both actresses grew accustomed to, but never fond of, having their lives in the spotlight. On Lohan's debut album, 2004's Speak, the single "Rumors" is about the frequent gossip about her personal life. In the case of Taylor, who was arguably the first celebrity tabloid target, the publicity around her offscreen activities focused mainly on her physical appearance and romantic relationships, particularly her on-again, off-again love affair with Richard Burton.

Liz & Dick executives have said that one of the main reasons Lohan was cast to play Taylor is because both actresses have had issues with substance abuse and addiction. In December 1983, Taylor became one of the first celebrities to publicly enter rehab when she checked herself into the Betty Ford Clinic, seeking treatment for alcohol and prescription drug abuse. Lohan, meanwhile, has made the practice de rigueur, having been in and out of rehab since 2007, and arrested on charges including possession of cocaine and several DUIs. In 2010, a judge ordered her to enter the Betty Ford Clinic, where an employee later accused her of battery.

Both had weight issues and were subject to intense body scrutiny During her first marriage to Richard Burton, Taylor intentionally gained weight in an attempt to focus on her role as a wife and avoid getting film offers. (It didn't work.) Later, in the late 1970s, she again put on pounds as a result of her depression and entered a "fat farm" in Florida with a girlfriend. In 1987, Taylor released the dieting book Elizabeth Takes Off: On Weight Gain, Weight Loss, Self-Image and Self-Esteem. Lohan has faced similar scrutiny, but for the opposite reason. Tabloids have often called the actress too skinny and, when her weight has fluctuated, have attributed both her emaciated look and at times "puffy" appearance to drug use and partying. Lohan has also denied speculation that she had breast augmentation surgery.

Though Lohan offered to lend her support to Barack Obama's presidential campaign in 2008, she was turned down and, perhaps as a result, tweeted in 2012 that she was supporting Mitt Romney. Taylor, on the other hand, played a political role as the wife of Republican Sen. John Warner from 1976 to 1982. She helped the senator campaign in 1978 and was a frequent visitor to the U.S. Capitol during their marriage.

Taylor once said that her three great loves in life were Richard Burton, her third husband Michael Todd (who was killed in a plane crash in 1958), and jewelry. At the time of her death, her extensive collection was reported to be worth more than $150 million. Two of the more famous diamonds were a 33.19-carat Krupp Diamond (later renamed the Elizabeth Taylor Diamond), which she wore daily, and the 69.42-carat Taylor-Burton diamond, both of which were gifts from Burton. In a 2012 interview, Lohan said that one of the primary similarities between herself and Taylor was a love of diamonds. However, Lohan's interest in them may be a bit more nefarious. In 2009, she was the subject of a police investigation after $400,000 worth of Dior diamonds went missing from a photoshoot she was doing in London. Two years later, a jewelry store employee claimed she tried to steal a diamond earring from her shop.