I've started a small list of wines that doesn't have your bank account screaming "insufficient funds" (well, you'll need at least $15 in your account for this list). These wines can be easily enjoyed every night of the week. Save your crowd-pleasing wines for a more special occasion rather than Tuesday night pizza night (as Steve Thurlow would say). Walking through the liquor store, you can easily find wines that aren't very expensive, but it's a bit harder to uncover the ones that will also give you an enjoyable tasting experience.
This list is just a start and I'll try to update it as I make my way through the ocean of wines to try! These are wines that I've tasted and have enjoyed for the small amount of money that they cost. Some more than others but wine is all about personal taste. I found that the selections below offer a bit more complexity in this price category.
For those in Ontario, some of these may be General List at the LCBO (meaning that they will most likely have them in stock all year) and others may be in Vintages (meaning that they will only be in stock for a short while, but may come back again the next year). If you like a wine, pay attention to the region that it's from. From that, you can start experimenting with other producers from that same region. Personally, I'm a huge fan of Southern France. You can usually find great value and taste in wines labeled "Cotes du Rhone, Cotes du Rhone Villages and Cotes du Roussllion-Villages". Wines from Chile are also great value for the most part. Chile has near-perfect conditions for grape growing and their wine industry is only getting bigger and better.
Caliterra Cabernet Sauvignon (Chile) $10.95
Chateau de Jau (France) $14.95
Chateau Bel Air (France) $11.95
Pey la Tour (France) $14.75
Calvet Medoc (France) $13.95
Sibling Rivalry Red VQA (Canada) $13.95
Paroles De Femme Cotes Du Rhone (France) $15.00
Concha Y Toro Winemaker's Lot No.11 Riesling (Chile) $14.95
Lacheteau Les Loges Vouvray (France) $14.95
J. Bouchon Sauvignon Blanc (Chile) $10.95
Chateau De Quincay Sauvignon (France) $13.95
Mouton Cadet Blanc (France) $13.25
Hillebrand Artist Series Unoaked Chardonnay (Ontario) $10.95
Hillebrand Artist Series Sauvignon Blanc (Ontario) $11.95