Should Have Been Bigger: Lindsay Lohan’s “Bossy”
In this franchise, we look back on songs that deserved a little more love and attention.
The year was 2008. The mid-aughts wild child and starlet Lindsay Lohan was seemingly getting her act together after a slew of personal and legal issues involving everything from drunk driving to a rehab stint. And after two successful, very ’00s pop-rock albums, including her daddy issues exposé “Confessions of a Broken Heart (Daughter to Father)” single from 2005, the then 22-year-old Mean Girls star was gearing up for a comeback.
That’s why when “Bossy,” written by R&B singer-songwriter Ne-Yo, leaked and later dropped in May, critics were stumped. While the synthy dance track played on everyone’s MySpace page, the song’s reception was mixed. People were expecting Lohan to continue on the alt-pop rock route. It was 2008 after all, and even Lady Gaga’s synth-pop hit “Just Dance” had to wait until January 2009 to explode in the States. A lot of people didn’t get it and audiences weren’t yet ready for LiLo’s jump on the mainstream electro-pop wave that ensued the following year.
In 2017, “Bossy” would just be called “Boss.” “I’m just a little bossy, I like it how I like it when I like it and that’s how it is,” Lohan confidently declares on the chorus. At a time when her contemporaries sang about love and relationships, she was unapologetically singing about power and confidence. Musically and lyrically, “Bossy” was ahead of its time. Commercially, “Bossy” peaked at number one on the Billboard Hot Dance Club Play chart, but that was it — no Hot 100, no heavy radio play, no promotion, and a shitty music video that seemed more like an afterthought.
Focusing on her then relationship with DJ Samantha Ronson and a clothing line, “Bossy” sunk into oblivion, and with it, Lindsay’s promised third album. After that, the actress went back to her hot mess antics and her singing career fell to the wayside. Lohan tragically succumbed to Hollywood’s dark side, but “Bossy” is a stellar reminder of the what-could-have-been had American listeners been that much more receptive to its glory. Listen to the original (and best) version of the song below.