Some most intriguing images found on the NYDL Digital Collection. All are undated, so any additional expert information or arbitrary guesses are welcome! My own tentative deductions below:
1.
"Distinguished scholars of our schools.—Edward Everett Horton, pupil of Grammar School No. 9, Courtland Street, Baltimore, MD."
That would make it a local Baltimore paper, and given EEH's timeline, the clipping would be ca. 1901/1902? (He graduated from Baltimore City College in 1904.)

2. and 3.
No information on the site about these photos, which I assume to be from a revue given at one of the Baltimore schools. Female roles played in drag, of course, as they did at all boys' schools. It's difficult to say with certainty because of the low resolution, but in the group photo I take it that EEH is the lady seated second from left, as the same character seen in the solo shot.
And the rest is history ...

