Songfacts®:

• "Bossy" was written by Ne-Yo together with the Norwegian production team Stargate. It was released as a single in 2008 and intended for Lohan's third album, Spirit In The Dark, which never materialized. Lohan was in rough shape around this time, constantly in the news for various arrests and misdeeds. She was just 21 but had been hitting the clubs for years, and had developed substance abuse problems. This adds an unfortunate subtext to the song, as Lohan sings:
  
  If I want it, I get it now
  
  Lohan did pull it together, but it took a while; she got sober around 2014 and managed to keep incidents at bay from that point forward. Her music career moving forward was mostly restricted to songs she worked on for her films.
• Ne-Yo told People magazine that the song is about strength. He explained: "It's basically about a woman being strong enough to get what she wants when she wants it. In this case, 'Bossy' is a term that describes confidence and power."
  
  And he wasn't thrilled with Lohan singing it, at least at first. The R&B singer-songwriter explained to Billboard magazine: "I gotta admit, we were like... Lindsay Lohan?' I mean, I've written for Beyonce, Mary J. Blige, Rihanna, Celine Dion and... Lindsay Lohan? But I will say this; we gave her a quality record and she did a ridiculously fabulous job. I was so shocked I had to call her and apologize for what I was thinking because she did so good. I think the world is gonna be surprised."
• The song took Lohan into the realm of electronic dance music. It got some play in the clubs and went to #1 on Billboard's Hot Dance Club Play chart.
• "Bossy" was the theme song to Lohan's 2019 MTV reality series Lindsay Lohan's Beach Club, set at her club in Mykonos, Greece. It ran for 12 episodes.