A linear structural model was studied to investigate the factors affecting reading literacy and mathematical literacy skills of 15-year-old students in the Programme for International Student Assessment (PISA) 2000 data across different cultural settings. Brazil, Japan, and Norway were selected for the purpose of comparison on the basis of their rankings in the PISA 2000 study. The factors studied were attitudes towards reading, student-teacher relations, classroom climate, communication with parents, use of technology, attitudes towards mathematics, and reading literacy. The results indicated that the latent independent variable with the strongest effect on mathematical literacy is the use of technology in Brazil, communication with parents in Japan, and attitudes towards reading in Norway. In all the three countries, reading literacy has the strongest effect on mathematical literacy skills; mathematical literacy has a stronger relation to attitudes towards mathematics; attitudes towards reading is negatively related to mathematical literacy measures but positively related to reading literacy measures, and finally, communication with parents has a positive relation with reading literacy skills. A disciplined classroom environment fosters more success in PISA tests in Japan; on the other hand, in Brazil a reversed result is found for this particular variable. The use of technology has a strong influence on reading skills in Brazil; however, no and negative effects of this variable are observed in Norway and Japan respectively. These findings are discussed with reference to cultural context.