What lead singles worked that are considered risky. The first one that comes to mind for me is "Gimme More" by Britney Spears and it also set the trend for the current state of music.
Ones that didn't work. Triumphant by Mariah Carey unfortunetly
I'd say We Found Love was kinda risky.
I mean, people are accustomed to Rihanna having huge songs with screaming/belting choruses.
This relied on an instrumental hook and a relatively unknown(in the US) producer.
It was the single that set her apart from the rest of the R&B world of music. It dropped all the fancy R&B instrumentation for a simple & soft pop-rock one. Shes the queen.