Migraine: The patient's symptoms of headache, sensitivity to light, ringing in the ears (tinnitus), and nausea are classic for migraine. The patient has a history of migraine, which further supports this diagnosis. The fact that the headache has persisted since Friday and has not responded to naproxen or tylenol also points towards a migraine, especially given the patient's history of using these medications.

Tension Headache: Given the patient's description of headache/pressure and the lack of response to initial treatments, a tension headache could be considered, especially if the patient is experiencing stress or anxiety, which could be exacerbated by their unspecified anxiety disorder.
Medication Overuse Headache: The patient is taking naproxen and has a history of long-term NSAID use, which could contribute to medication overuse headaches, especially if the patient is taking these medications frequently for headache relief.
Sinusitis: The patient's symptoms of headache and sensitivity to light could also be indicative of sinusitis, especially if there are other symptoms such as facial pain or nasal congestion, which are not mentioned but could be explored further.

Subarachnoid Hemorrhage: Although less likely given the patient's presentation and history, a subarachnoid hemorrhage is a critical diagnosis that must be considered in any patient presenting with a severe headache, especially if it is described as "the worst headache" of their life. The patient's symptoms do not strongly suggest this, but it cannot be entirely ruled out without further evaluation.
Temporal Arteritis: This condition, although more common in older adults, can present with headache and should be considered, especially if there are other symptoms such as jaw claudication or visual disturbances.
Intracranial Hypertension: Idiopathic intracranial hypertension (IIH) can cause headaches that are worse in the morning, worsen with coughing or straining, and are associated with vision changes, which are not explicitly mentioned but could be relevant given the patient's sensitivity to light.

Trigeminal Neuralgia: This condition causes intense pain in the face and could potentially cause headache, though it is less likely given the patient's description of their symptoms.
Occipital Neuralgia: Involves the nerves that run from the base of the skull to the scalp and can cause headache, though it is not as common and would typically present with more localized pain.
Cervicogenic Headache: Originates from the cervical spine and its structures, which could be a consideration given the patient's history of neck and joint issues, though it is less directly related to the patient's current symptoms.