Studies have demonstrated that anthocyanins can function as antioxidants, reduce inflammation, and improve dyslipidemia. Tart cherries are anthocyanin-rich, making them particularly attractive as a functional food to improve cardiovascular disease (CVD) risk. There have been few published studies to date examining the impact of tart cherries on biomarkers of dyslipidemia and inflammation, particularly in overweight and obese individuals at high risk for these conditions. This study evaluated the effect of consuming 100% tart cherry juice daily on blood lipids including total cholesterol, low-density lipoprotein cholesterol (LDL-C), calculated very low density lipoprotein cholesterol (VLDL-C), triglycerides (TG), high density lipoprotein cholesterol (HDL-C), and the CVD risk ratios, as well as the inflammatory biomarkers interleukin 6 (IL-6), interleukin 10 (IL-10), tumor necrosis factor-alpha (TNF-alpha), C-reactive protein (CRP), monocyte chemotactic protein-1 (MCP-1), and erythrocyte sedimentation rate (ESR) following a 4-week period. Based on the high anthocyanin content of tart cherries, it was hypothesized that the lipid and inflammatory profiles would be significantly improved following the intervention. A total of 26 men and women completed this 4-week randomized, single-blind, placebo-controlled, crossover study. Participants were randomized to drink either 8 ounces of placebo beverage or tart cherry juice daily for 4 weeks. Following a 4-week washout period, the alternate beverage was consumed. Ultimately, this investigation demonstrated no statistically significant alterations in any of the lipid or inflammatory biomarkers when analyzed across time and between interventions (p > 0.05). As expected, glucose and insulin parameters remained stable over the duration of the study, as well as self-reported physical activity level, total calorie consumption, and macronutrient intake. However, trans-fat was reported to be significantly higher during the cherry arm of the study as compared to the placebo arm (p < 0.05), potentially confounding other results. Although the results of this study were equivocal, it is feasible that a higher dose, longer treatment duration, or more susceptible target population may be required to elicit significant effects. Consequently, further investigation is necessary to clarify this research.