The ad, created by Saatchi & Saatchi, sees Bacon shuffling through Apple Music in search of the perfect song, before landing on Britney Spears' Oops!...I did it again.
He also strips out of his usual black leather jacket and jeans to reveal his actual outfit – the red latex suit worn by Spears in the original music video (below)
Spears herself appears to tell Kevin he shouldn't be rifling through her wardrobe. "Oops," he says, in a somewhat predictable punchline.
The deal marks Apple Music's first bundle deal with a UK operator, and signals the company's efforts to market its music streaming service to the mainstream. Apple already has a bundle deal with Telstra in Australia, while rival Spotify signed up with Vodafone in 2013. Deezer has a deal with Three.
Apple Music lags Spotify in terms of paying subscribers and carrier partnerships are one way of boosting reach and numbers. Last month, Apple announced 13 million paying subscribers, compared with Spotify's reported 35 million.
The partnership gives new or upgrading EE customers free access to Apple Music for six months from 1 September, even if they are already subscribers.
The ad was created by Ben Mills and Matt Butterfield at Saatchi & Saatchi and directed by Hank Perlman through Hungryman.
Havas Sport & Entertainment Cake is the lead partnership agency, which brokered the deal with Spears on behalf of EE, and media is handled by MEC.
The ad runs for one month from today, featuring during The X Factor on ITV. Creative also runs on print, video-on-demand, outdoor, digital and across social media.