Among the various news genres, the distinctive telegraphic syntax and stylistic features of newspaper headlines have drawn a good deal of linguistic attention. However, no substantive analysis has been conducted to compare English headlines published in native and non-native contexts. To this end, the present study was done in two phases. In the first phase, 2000 English headlines were randomly selected from the electronic versions of New York Times (1000) and Tehran Times (1000) and analyzed syntactically and stylistically based on Haixin's (2003) model. Results indicated differences in syntactic and stylistic features of the headlines of the two newspapers. In the second phase, 26 male and female senior BA students of English were asked to translate 60 headlines chosen from the two newspapers. The analysis of the translations revealed that, in general, the participants experience greater difficulty comprehending and translating English headlines of New York Times, suggesting contextual variations being important in comprehending and translating headlines.