Chronic pain states have resulted in an over-reliance on opioid pain relievers, which can carry significant risks when used long-term. As such, alternative pain treatments are increasingly desired. Although emerging research suggests that cannabinoids have therapeutic potential regarding pain, results from studies across pain populations have been inconsistent. To provide meta-analytic clarification regarding cannabis’s impact on subjective pain, we identified studies that assessed drug-induced pain modulations under cannabinoid and corresponding placebo conditions. A literature search yielded 25 peer-reviewed records that underwent data extraction. Baseline and end-point data were used to compute standardized effect size estimates (Cohen’s d) across cannabinoid administrations (k = 39) and placebo administrations (k = 26). Standardized effects were inverse-variance weighted and pooled across studies for meta-analytic comparison. Results revealed that cannabinoid administration produced a medium-to-large effect across included studies, Cohen’s d = −0.58, 95% CI (−0.74, −0.43), while placebo administration produced a small-to-medium effect, Cohen’s d = −0.39, 95% CI (−0.52, −0.26). Meta-regression revealed that cannabinoids, β = −0.43, 95% CI (−0.62, −0.24), p < 0.05, synthetic cannabinoids, β = −0.39, 95% CI (−0.65, −0.14), p < 0.05, and sample size, β = 0.01, 95% CI (0.00, 0.01), p < 0.05, were associated with marked pain reduction. These outcomes suggest that cannabinoid-based pharmacotherapies may serve as effective replacement/adjunctive options regarding pain, however, additional research is warranted. Additionally, given demonstrated neurocognitive side-effects associated with some constituent cannabinoids (i.e., THC), subsequent work may consider developing novel therapeutic agents that capitalize on cannabis’s analgesic properties without producing adverse effects.