My absolute favorite class to play in a non computer version of DnD is the bard. It has the most character by nature. I have more fun playing a bard than any other character. Typically I enjoy the role playing aspect of…well…role playing, so the bard is perfect. Bards have high charisma which is useful for plenty of mostly useless tasks like lying or negotiating, yet I never get enough. If the DM does not supply me with ample opportunity to use my skills I usually invent one like trying to woo a drow mage during combat and declaring to her my true love and undying devotion up to the point when the party kills her. Love is fleeting.
In forth edition there are some more useful things that bards can do but remain the “jack of all trades” they were designed to be. Personally I enjoy the lying, cheating, and negotiating the bard is capable of. I regularly enjoy telling the party to engage in something everyone knows isn’t a good idea and then when they disagree rolling a “diplomacy” check. It usually sounds something like this:
Me: “Hey everyone, let’s go ask the leader of the evil guild if he knows anything about the noble’s daughter disappearing”
Party member: “That’s dumb. If it was him why would he tell us?”
Me (roll diplomacy 1d20+17) 17+17=34
party member: (rolls insight 1d20+5) 15+5=20
Party member: “You’re right, good idea”
I love it. Way more fun than asking the super nice priest about it.
I also enjoy making my characters after an actual musician. The most recent was Rick James. The DM suggested that I make it a bit more “DnD” and spell it “Rhyk Jaimes” or something but that never really took hold. Instead I ran around saying “Rick James Bitch!,” and singing “Superfreak” whenever the party needed and inspirational song. It was great. I loved every minute.
I also really enjoyed the optional “at will power” available to bards, “vicious mockery.” I decided that my character would say a “your momma” joke every time he used the attack. It was a lot of fun to tell an ogre “Your momma so fat that even Dora couldn’t explore her.” It turns out that many creatures one might encounter in DnD are sensitive about their mommas. It was a blast. I love bards so much that I have to be discouraged from playing one every time. Apparently too much of a good thing is bad. That or everyone was tired of the momma jokes. Oh well, guess I’ll have to play a boring ole elf wizard. No fun at all.