518 E. Main St., El Cajonwww.members.cox.net/rzbar/catdaddys.htmA self-proclaimed “dirty old man place,” Cat Daddy's is as unpretentious as they come. On their website, they brag: “Some good customers, Very Sexy bartenders, Good management, Live music.” Go there and let us know if it's all true.
8365 La Mesa Blvd., La Mesawww.centifontis.comIf your main purpose for coming to Centifonti is to tackle the infamous Beer Boot, keep your eyes straight ahead until you reach the bar and are staring at the box of Flutie Flakes. If you're not in the drinking mood, or you just want to make the Beer Boot an even bigger challenge, let yourself be seduced by the selection of sweets to your right, including malt-ball-covered candy apples and homemade ice-cream sandwiches.
7366 El Cajon Blvd., La Mesawww.chicoclub1940.comOne of San Diego's oldest bars has somehow become a “pirate bar,” whatever that means. We're guessing it's college-kid slang for “cool dive.”
7664 Broadway, Lemon Grove619-469-6344Get your kicks at your own risk at this East County watering hole. Thanks to its primo location—in front of a GTM Discount store and next to a porn shop—it creates an East County Bermuda Triangle of sorts, where many enter, but very few leave. Don't say we didn't warn you.
El Cajon Grand
437 E Main St. El Cajon619-749-7355All the cool kids are flocking to the Grand, with its flashy new interior and flat screens galore. But keep in mind this is El Cajon, so when we say “cool kids,” we mean the ones with ultra-white flat-billed caps and sneakers to match, sporting at least one tribal tattoo and driving a lifted truck that proudly displays a set of Truck Nutz.
8384 La Mesa Blvd., La Mesa619-462-9100Located in the unexpectedly adorable La Mesa Village, Gio is a casual yet classy wine bar with interior design playing upon an interesting wine-barrel theme. Try some tapas and have bar manager Ryan recommend a glass from the impressively extensive list.
3315 Buena Vista Ave., Lemon Grove619-469-1190A beer-and-wine bar frequented by Lemon Grove locals, but don't wander in thinking you'll find a vintage Cabernet and a rare, imported brew. Good place to knock back a few High Lifes on a Wednesday afternoon after getting back from the unemployment office.
Hooley's Irish Pub & Grill
2955 Jamacha Road, Suite 21, Rancho San Diegowww.hooleys.comWhat do you get when you cross a classic Irish dish with a San Diego specialty? Corned-beef tacos at Hooley's. Just add beer.
1185 E. Main St., El Cajon619-442-0258Picture the nightly karaoke at The Lamplighter. Now add a few cowboys and a popcorn machine.
Main Tap Tavern
518 E. Main St., El Cajonwww.maintaptavern.comThere's a crap-ton of beers here. The staff is friendly and knowledgeable, and while you wait for your brew, you can admire the ornate glass tap handles. When it's NFL season, Main Tap opens at 10 a.m. and offers free hot dogs and happy-hour prices all day.
Mr. G's Tavern
7081 University Ave., La Mesa619-469-3834 Mr. G's Saturday-night karaoke is a local favorite. Spend (lose) the money you save on the cheap drinks at the Lotto scratcher vending machine in the corner.
6149 Lake Murray Blvd., La Mesa619-464-9119This tiny hole-in-the-wall offers the company and encouragement necessary for consuming alcohol at 6 a.m.
Riviera Supper Club & Turquoise Room
7777 University Ave., La Mesawww.rivierasupperclub.comThis cook-your-own dinner spot has one of the coolest lounges anywhere in the county. Even if it's crowded, stick around and make sure to order one of the signature cocktails—it'll knock you on your ass.
7030 University Ave., La Mesa619-668-1256Shenanigans' Twitter feed inspires deep thought. For instance, on July 25, there was this one: “now features Seagrams Sweet Tea Vodka, $4.25.” (Try wrapping your mind around “sweet tea vodka”). And, we've yet to puzzle out July 3's Tweet: “Missy doesn't like tomatos.”
Thornton's Irish Pub
1221 Broadway, El Cajonwww.thortonsirishpub.comLive music on the weekends promises a crowd, and an El Cajon crowd promises great people-watching.
The Wagon Wheel
8861 North Magnolia Ave., Santee619-448-8550Everything you would expect from a Santee bar called The Wagon Wheel. A hearty blend of country music and hip-hop provide the soundtrack to beer pong and “Rock, Paper, Scissors” tournaments on Tuesday nights.