Medieval painting is much more frequent than sculpture. Rupestrian churches offer a wide collection of paintings, realized between the 9th and the 15th centuries, and with more frequency between 12th and 14th centuries.
Some icons on tables were imported from Constantinople or Crete: rupestrian churches still present the bare original locations of these tables, and some of these icons have been transferred to new churches when rupestrian churches were abandoned. The frequent subject of these icons is Maria, the Odegitria, the Glicofilusa and the Galattotrofusa; a prototype of these icons is in the Episcopy of Andria, which has been replicated many times by local painters. There are also Christological icons, as the Pantocrator, and scenes from the Passion, or pictures of Saints on thrones, as Saint Joan the Merciful and Saint Joan the Evangelist and Saint Knight as Saint George.
Wall Paintings represent the greatest expression of rupestrian painting: there is no doubt about their provenience, as they were realized where they are now. The only subject for frequent debates among the researchers is influence and derivation, starting from personal style analysis. Researchers try to delineate the figure of artists, which are generally unknown. Only few painters are known, as Eustazio and Teofilatto, who realized two figures of Christ in Carpignano Salentino, in 959 and in 1020, and Giovanni, who defined himself as a “poor painter” in a hypogeal church in Taranto. Painters generally never signed or dated their works: the two above mentioned paintings and a painting from 1321 in Déisis on the apse of Santa Marina in Massafra (Taranto).
Paintings in southern Italian rupestrian churches mostly represent icons, single figure of Saints, and were committed for devotion. The single devote asked for the representation of his favourite Saint, no matter if there was another painting of the same Saint in the same church: in the church of Santa Marina in Massafra (Taranto) the Saint Patron of the church was painted three times between the 12th and the 13th centuries, twice with an exegetic Greek inscription, and once with the Latin name, Margarita.
Cycles of Ancient and New Testament (which were painted in great monastic churches of Cappadocia) are not present, due to the kind of committeemen and the lack of a decorative program. Isolated episodes were painted, as the Original Sin (in Matera and in Castellaneta), the rare Sacrifice of Isaac (in Massafra), the Last Supper (very rare, in Massafra), the Crucifixion (which was very common in the Late period) and the Deposition from the Cross (very rare, in Massafra). In Salento, a late ingenuous but expressive unicum is the Virgin on a background of stars, with visions from the Apocalypse.
Paintings were the reflection of popular devotion: this is why the images of the Virgin were very common (more as Odegitria¸ Galattotrofusa and Glicofusa, but there are also rare images of the Virgin conducting by hand the Holy Child with a basket full of eggs, as in the church of Candelora, Massafra). Chirst was represented in many apses as the Judge of the Final Judgement, in the Déisis, with the Virgin and Saint Joan the Baptist. Often, the figure of the Baptist was substituted with the patron Saint of the committer. The most painted Saint is the Saint Bishop Nicholas of Mira, who was worshipped in Puglia before the relics arrived in the Region. There are also very rare representations of his life: in Mottola, there is the painting of the episode in which the Saint redeems three girls whom their poor father wanted to prostitute. There are also Auxiliary and Knight Saints, as George, Eustachio, Theodore, and military Saints, other Virgins (as Parasceve/Venerdì, Lucy and Catherine of Alexandria), the Fathers from Cappadocia (especially Basilio, sometime flanked by Benedetto, the patriarch of western Monks) the great Anchorites and Hermits (as Onofrio, Paolo and Antonio Abate) the Apostles (especially Paul, after the 9th century when the Normans and the Schism made necessary to declare the support to the Church of Rome, in fear of future repressions).
The image of Michael the Archangel is very common, whose cult and iconography derives from the Apocalypse. He is often represented with wings, armour, sword or lancet, defeating the Demon/Drake. Sometimes he holds a scale to weigh souls (psychostasis), as in the Islamic tradition and with no link with the Christian tradition. The book of the Apocalypse was the source for later books, which were dedicated to the figure of the Archangel: these books defined him as a majestic being with the power of examinating souls before the Final Judgement. The Byzantine iconography is more common in rupestrian churches, so the Archangel is more represented as a Court dignitary (with the loron) with the title of Archistratigos (a Commander in chief) than the western figures of a warrior fighting against the Demon, or while weighing souls. The image of Gabriel the Archangel is rarer, though he is present in some Annunciation.
The studies on rupestrian iconography are still very few. Critical contributions on rupestrian paintings have been focused on the analysis of formal factors, in order to set the chronology and to identify the artists within the wider Byzantine wall painting. Rupestrian painting is a small aspect of the whole Byzantine wall painting, as it is a private commission for private use. The risk is to skip from an old wrong pan-monastic idea to an equally wrong pan-funerary conception. In the last three decades, the rising archaeological research is going much further than the old historical and artistic vision.