Photos of Sri Aurobindo tend to cluster in two groups; those from his younger period, prior to 1920 (mostly the period from 1907 to 1915, when he was in his mid 30s to mid 40s , and those when he was much older, dating from 1950, when he was in his late 70s. The difference between Sri Aurobindo's energy in these two lots of photos is profound.
The earlier photos show Sri Aurobindo as a charismatic and handsome figure. They include posed portraits from Sri Aurobindo's days as an academic at Baroda college or from that period, some from his revolutionary days in Calcutta, others mug shots from his imprisonment at Alipore jail, and some from his early Pondicherry period (the 1910s). This latter period marked the initial and fast progressing stages of his yoga (his notes since published in Record of Yoga) and the period of writing almost all of his major works (only Savitri was written later), which were published in serial form in Arya journal. This was Sri Aurobindo at his prime, before the full resistance and difficulty of realising the Supermind was encountered.
Mention should be made here of two very similar photos, both dating from the period from around 1915. One, heavily retouched, has been widely reproduced, and shows a hagiographic figure, with glossy shiny hair, and dreamy eyes. The face is totally lacking in shadow and texture, and resembles a latex doll, rather like airbrushed photos of Playboy girls. This hagiographic image seems to fill the same role in the Integral Yoga community as the iconic and equally hagiographic portrait of Che Guevuera serves for 1960s and 70s revolutionaries, or the pious dreamy blonde Jesus of endless numbers of bible tracts and Sunday school books.
Peter Heehs was the first to point out how unrealistic this image is, as mentions it at the start of his classic academic biography The Lives of Sri Aurobindo. Heehs contrasts it with the following image, which he points out did not even appear in print before 1976, the year he published it in an ashram journal:
I agree with Heehs that this "warts and all" photo is infinitely superior. It shows the real Sri Aurobindo, a powerful and striking figure, not at all dreamy, his pockmarked skin and lined face showing him to be a real human being, rather than a dreamy and idealised Christ-like figure. I am intersted in the real Sri Aurobindo, a Realised being who nevertheless was still a historical figure with srengths and weaknesses, rather than an imaginal ideal like the Jesus and Krishna or religion.
The 1950 photos were taken shortly before Sri Aurobindo's death, by Henri Cartier-Bresson, the father of modern photojournalism. (see the essay The Decisive Moment by Michael Miovic).
The later photos portray a very different Sri Aurobindo to the earlier ones. Whilst artistically profound, and revealing the real, historical, Sri Aurobindo rather than an idealised saint-image, they show (so it seems to me, and to friends who have also mentioned this to me, although devotees of Sri Aurobindo and the Mother may disagree) a man listless and worn out. This has nothing to do with age and surface wrinkles, the Mother even when older always looked full of life; every photo emanating grace and power. The same applies to images of other adepts. Photos of Ramana Maharshi, Nityananda, Andanamyi Ma, Yogi Ramsuratkumar, and other authentic Realisers always convey great power, serving as a window to the Supreme, regardless of whether they refer to the Realiser when physically young or old. They show a figure alert and alive, radiating power and charisma, engaging with the viewer even through the medium of the fixed two-dimensional image.
The reason for this is that these later photos were taken only a few months before Sri Aurobindo died. He was already ill with prostate cancer, and had decided he was going to leave his body this time, rather than heal himself as he had with previous illnesses. According to Mirra's account in the Agenda, Sri Aurobindo had to leave his physical body for the sake of the yoga. The reasons for this are esoteric rather than rational, and cannot be clearly explained in logical terms.