I don't know how, but a LOT of my students in the 8th grade still can't tell time on an analog clock when they get to me (Really?! How is that even possible?)
The only clock I have in my classroom (and will EVER have in my classroom) is an analog clock.
I reference the clock daily and talk about how to read it daily. I will walk over to the clock and point to a time and tell the kids, "Okay, my little Sea Anemones, you have until 10:40 to work on this and then we move forward!"
I do this consistently and they do eventually get it, but at the start of the year I like to use fun countdowns as well.
I found this site and ADORE it (So do the kids):
They have great animated countdown clocks that you can project on your Smart Board.
These are screen shots of my kids' favorite timers:
WARNING:If you choose the race/swimming choice, your kids will pick their favorite and get entirely too sucked into who will win the race in the last 30 seconds or so of the timer!