Previous studies have yielded inconsistent results when documenting the association between key dietary factors and adolescent weight change over time. The purpose of this study was to examine the extent to which changes in adolescent sugar-sweetened beverage (SSB), diet soda, breakfast, and fast-food consumption were associated with changes in BMI and percent body fat (PBF). This study analyzed data from a sample of 693 Minnesota adolescents followed over 2 years. Random coefficient models were used to examine the relationship between dietary intake and BMI and PBF and to separate cross-sectional and longitudinal associations. Adjusting for total physical activity, total energy intake, puberty, race, socioeconomic status, and age, cross-sectional findings indicated that for both males and females, breakfast consumption was significantly and inversely associated with BMI and PBF, and diet soda intake was significantly and positively associated with BMI and PBF among females. In longitudinal analyses, however, there were fewer significant associations. Among males there was evidence of a significant longitudinal association between SSB consumption and PBF; after adjustment for energy intake, an increase of one serving of SSB per day was associated with an increase of 0.7 units of PBF among males. This study adds to previous research through its methodological strengths, including adjustment for physical activity and energy intake assessed using state-of-the-art methods (i.e., accelerometers and 24-h dietary recalls), as well as its evaluation of both BMI and PBF. Additional research is needed to better understand the complex constellation of factors that contribute to adolescent weight gain over time.