"why am i phoenix wright such a great lawyer"

Stand Up Comedy

Neil Hamburger has spent his career pretending to be what may be the world's worst comedian.

Film

A famous case is The Lion King, where this is the main appeal of Timon's character. His jokes are so lame you can't help but chuckle- this was intentional of course. Hakuna Matata has this:

Game Show

The Unknown Comic on The Gong Show did this deliberately. Watch him here.

Literature

Jack Aubrey in the Master and Commander series makes a lot of terrible puns, and often gets them wrong since he's an inveterate Malaproper, but he delights so much in his own jokes that it's hard not to laugh with him.

Live-Action TV

Sarah Silverman on The Sarah Silverman Program. She puts a crying baby on a branch outside during her baby shower so she can deliver the punchline to her joke about how she lost a pair of chopsticks: "I'm like, 'Silver-WHERE?'"

New Media

Similarly, Bubs did a standup routine during one of the Halloween cartoons. "And remember, like, ten years ago? People's clothes looked funny! And the music sounded terrible!"

Theatre

Harry in The Time of Your Life wants to be a great comedian, but nobody laughs at his comic monologues.

Who is Jack Aubrey?

Jack Aubrey in the Master and Commander series makes a lot of terrible puns, and often gets them wrong since he's an inveterate Malaproper, but he delights so much in his own jokes that it's hard not to laugh with him.

What is Timon's famous case?

A famous case is The Lion King, where this is the main appeal of Timon's character. His jokes are so lame you can't help but chuckle- this was intentional of course. Hakuna Matata has this:

Who is the girl who puts a crying baby on a branch outside during her baby shower?

Sarah Silverman on The Sarah Silverman Program. She puts a crying baby on a branch outside during her baby shower so she can deliver the punchline to her joke about how she lost a pair of chopsticks: "I'm like, 'Silver-WHERE?'"

What are some examples of Deadpan Snarker?

Deadpan Snarker radio satirists Bob and Ray often pursued aggressively unfunny material to its logical limit and beyond, as a way of "seeing what [they] could get away with." Notable examples include the fifteen-minute, multi-show "Bulgarian Cream Pie" bit and an instance of a grouchy Bob Elliott playing intentionally annoying music because he had to broadcast alone on Christmas Day.