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The skeletal system is a common target of glucocorticoids. Structural and functional impairment of skeletal system is a relevant cause of morbidity and disability in patients with Cushing's syndrome. Thirty-six patients long-term (3.9 ± 0.5 yrs) cured from Cushing's disease (CD), 26 with adulthood-onset CD (AOCD) and 10 with childhood-onset CD (COCD) and 2 groups of controls, 24 age- and sex-matched patients with nonfunctioning pituitary adenomas (NFA) and 36 age- and sex-matched healthy subjects (HS), entered this open transversal controlled study to evaluate the prevalence of spine abnormalities and damage by standard radiography in subjects with a history of Cushing's syndrome. Symptoms and signs of backache were present in 86.1% CD patients (100% COCD and 80.8% AOCD), in 30.5% HS (χ2 = 20.6, p < 0.0001) and 37.5% NFA patients (χ2 = 13.2, p < 0.0001). The prevalence of trabecular bone rarefaction (χ2 = 6.5, p < 0.01 and χ2 = 4.5, p < 0.05), vertebral collapse (χ2 = 10.7, p < 0.01 and χ2 = 7.0, p < 0.01) and scoliosis (χ2 = 10.9, p < 0.01 and χ2 = 11.1, p < 0.01) resulted significantly increased in CD patients as compared both to HS and NFA patients. In CD patients, the number of collapsed vertebral bodies was significantly correlated to age of disease onset (r = −0.63, p < 0.0001), disease duration (r = 0.33, p < 0.05) and urinary free cortisol levels at disease diagnosis (r = 0.72, p < 0.0001). The prevalence of cortical bone sclerosis was significantly increased in AOCD than in HS (χ2 = 6.5, p < 0.01) and COCD (χ2 = 7.7, p < 0.01) whereas that of trabecular bone rarefaction was significantly higher in COCD patients than in HS (χ2 = 18.3, p < 0.0001), NFA (χ2 = 14.2, p < 0.0001) and AOCD patients (χ2 = 9.1, p < 0.01). Patients cured from CD have increased prevalence of spine damage, mostly when the disease developed before the completion of skeletal growth. Therefore, a periodical radiological follow-up of the skeleton and a specific treatment for the bone damage should be included in the management of patients with Cushing's syndrome.