News headlines often evoke sentiment by intentionally portraying entities in particular ways, making targeted sentiment analysis (TSA) of headlines a worthwhile but difficult task. Due to its subjectivity, creating TSA datasets can involve various annotation paradigms, from descriptive to prescriptive, either encouraging or limiting subjectivity. LLMs are a good fit for TSA due to their broad linguistic and world knowledge and in-context learning abilities, yet their performance depends on prompt design. In this paper, we compare the accuracy of state-of-the-art LLMs and fine-tuned encoder models for TSA of news headlines using descriptive and prescriptive datasets across several languages. Exploring the descriptive--prescriptive continuum, we analyze how performance is affected by prompt prescriptiveness, ranging from plain zero-shot to elaborate few-shot prompts. Finally, we evaluate the ability of LLMs to quantify uncertainty via calibration error and comparison to human label variation. We find that LLMs outperform fine-tuned encoders on descriptive datasets, while calibration and F1-score generally improve with increased prescriptiveness, yet the optimal level varies.