The use of handheld devices, such as smart phones for personal entertainment, has become commonplace in today's lifestyle. Virtually all of these devices are equipped with Bluetooth technology, which can be used to distribute entertainment content, such as music and movie clips. Mobile users can download content from opportunistically available infrastructure (e.g., digital billboards) and direct peer-to-peer (P2P) collaboration, which significantly increases content availability/coverage. P2P content distribution protocol design is heavily influenced by the characteristics of Bluetooth, which is a main departure from Internet-based content distribution. However, little has been done to understand the performance of overall Bluetooth operations, ranging from peer discovery to data downloading, in dynamic environments with mobility, interference, and different Bluetooth versions/chipsets. In this paper, we perform an extensive measurement study and find that Bluetooth-based content distribution suffers from time/energy-consuming resource discovery and limited bandwidth, even with the enhanced features of the latest Bluetooth version. Given this, we discuss strategies that can effectively improve the performance of the resource-discovery and downloading phases.