Gambling with the Devil is the twelfth studio album by German power metal band Helloween, released in Japan on 24 October 2007, and in Europe on 29 October. The single "As Long as I Fall" is download-only and was released in late September.

When asked about the album, bassist Markus Grosskopf commented:[1]

It was an album without any concept, but still we had that concept with that little game on it, that little "Crack the Riddle". [...] And then, that was nice, it was a great piece of work and when you do such an output like Keeper III it's like you've got to open your head and empty it at first, close it and then start thinking new for Keeper thing you know, but then it's very, very hard work. You've got to think very different from what you do when you just write the songs so to say, just like writing a normal metal song or rock song, it's very different. But that's what we did with the Gambling with the Devil and I feel very good just doing proper decent songs. You cannot do always like this concept thing. [...] It's never easy, but once you got an idea you don't have to think about "Oh, that's five minutes missing" you know. What do I put in to make it fit for the concept? Fit it to make it fit in the concept of something, it's just like if there's a song of five minutes or four minutes and it's cool, you don't have to think about how is it fitting in the concept, if the song's good the song's good, it goes on the record.

Band members
Andi Deris – lead vocals
Michael Weikath – guitar
Sascha Gerstner – guitar, backing vocals
Markus Grosskopf – bass
Dani Löble – drums
Guests
Biff Byford - spoken vocals on "Crack the Riddle"
Matthias Ulmer - keyboards