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Purpose. Examine how sociodemographic, health, behavioral, and health care utilization factors are associated with being obese or having diabetes among baby boomers and older adults. Design. Cross-sectional data were drawn from the 2007–2008 National Health and Nutrition Examination Survey. Setting. United States. Subjects. A sample of 3439 baby boomers and older adults included (mean age, 62 years). Measures. Covariates included sociodemographics, health outcomes, behaviors, and inpatient and outpatient health care utilization. Analysis. Multinomial logistic regression was used to explore which similar or different covariates were associated with different health states between baby boomers and older adults. Results. Approximately 8% of baby boomers and 10% of older adults had the twin diagnoses of obesity and diabetes. Having both obesity and diabetes was more common among baby boomers and older adults who were African-American (odds ratio [OR] = 1.79, p = .029 for baby boomers; OR = 3.45, p < .001 for older adults), perceived their general health as fair/poor (OR = 7.67, p < .001; OR = 4.13, p < .001), and utilized outpatient care more often (OR = 8.28, p < .001; OR = 5.35, p = .004). Being obese only was observed less among baby boomers who were current smokers (OR = .45, p < .001), whereas it was observed more among older adults who were former smokers (OR = 1.25, p = .046). Having diabetes only was observed more among baby boomers who had hypertension (OR = 2.44, p = .01), whereas it was observed more among older adults who had very high cholesterol (OR = 2.31, p = .029). Conclusion. Identifying chronic disease risk factors during middle age is important for ameliorating further complications in later life. Knowing more about the correlates of obesity and diabetes among different age groups can help health care planners better target preventive health care services.