Chocolate is generally considered a tricky ingredient to match but it's not that hard - unless it's a hot fondant pudding.
The usual suspects (sweet red wines) just don't seem to work as well so it occurred to me that maybe I should turn to a beer. The perfect candidate turned up in the form of the Bristol Beer Factory's Ultimate Stout a really delicious sweet malty brew with just a hint of espresso. It provided a refreshing counterbalance to a seriously sweet Waitrose Seriously Chocolatey pudding (with an added dollop of vanilla ice cream I have to confess) - for me the perfect match.
I'm conscious though it might not be for everyone and as I don't have a very sweet tooth I tried another couple of drinks with it - a Blandy's Duke of Clarence Madeira and a Barbadillo PX sherry. The Madeira was fine but the PX was better still, complementing the warm oozy chocolate with the rich taste of boozy raisins. I guess for most people that would be the star match though I'm still rooting for the stout which I also enjoyed recently with Stichelton (an unpasteurised version of Stilton cheese).