1929
Bosko, The Talk-ink KidA cartoonist (portrayed in live action by Rudolph Ising) draws Bosko, who comes to life. Bosko speaks, sings, dances and plays the piano before the cartoonist sucks him into his ink pen and pours him back into the inkwell. Bosko pops out of the bottle and promises to return.
Outback Buddy
That's a fake cartoon from the season finale of the first season of Animaniacs in The Warners 65th Anniversary Special. The Warner brothers were sidekick of Buddy, a character created to replace Bosko. The episode set this episode in 1929 but Buddy's first appareance is officially in 1933