Large Language Models (LLMs) have shown significant limitations in understanding creative content, as demonstrated by Hessel et al. (2023)'s influential work on the New Yorker Cartoon Caption Contest (NYCCC). Their study exposed a substantial gap between LLMs and humans in humor comprehension, establishing that understanding and evaluating creative content is key challenge in AI development. We revisit this challenge by decomposing humor understanding into three components and systematically improve each: enhancing visual understanding through improved annotation, utilizing LLM-generated humor reasoning and explanations, and implementing targeted alignment with human preference data. Our refined approach achieves 82.4% accuracy in caption ranking, singificantly improving upon the previous 67% benchmark and matching the performance of world-renowned human experts in this domain. Notably, while attempts to mimic subgroup preferences through various persona prompts showed minimal impact, model finetuning with crowd preferences proved remarkably effective. These findings reveal that LLM limitations in creative judgment can be effectively addressed through focused alignment to specific subgroups and individuals. Lastly, we propose the position that achieving artificial general intelligence necessitates systematic collection of human preference data across creative domains. We advocate that just as human creativity is deeply influenced by individual and cultural preferences, training LLMs with diverse human preference data may be essential for developing true creative understanding.