Specimens of human skulls belonging to individuals who underwent awake surgeries have been found across the world and some of them date back to 12,000 years ago, witnessing historically remote awake procedures. More contemporary advances were initially provided by the contribution of Penfield, with the discovery of the “homunculus motorius,” and later from Ojemann, with the first fine awake intraoperative mapping of the language functions. Awake surgery stands as the definitive approach to maintain the neuro-oncologic balance, namely preserving the function while maximizing the extent of resection, in lesions located in eloquent cortical and subcortical structures. Awake surgery offers the unique possibility to intraoperatively investigate highly complex eloquent networks such as those exerting motor and language functions, and possibly, through appropriate stimulation and testing executive and praxis functions either. Intraoperative neuromonitoring is a critical part of Awake surgery: the different techniques comprise electroencephalography, electromyography, sensory and motor evoked potentials and most importantly direct cortical stimulation, which is crucial during the intraoperative testing to “draw” the map of the function in case of positive mapping or rule out functional spots in negative mappings. Neuropsychology is crucial either: its contribution involves the preoperative, intraoperative, and postoperative periods and despite the lack of consensus and standardization concerning the intraoperative psychometric tools, coupled with intraoperative neuromonitoring it provides critical data concerning the integrity of the cognitive function and about the general functional outline. Awake surgery appears to be still, to date, the gold standard approach to intraoperatively investigate cognitive functions in selected and eligible patients.